2-Formylbenzoic acid

Reaction of 2-formylbenzoic acids with 1, 1-bisdialkylaminoethylenes in acetic anhydride has been found91 to yield phthalides such as 21. These color formers are claimed to yield blue to green images, but have also been described92 as intermediates for the preparation of divinyl phthalides by a route identical to that described in Scheme 3, for which they are probably of more significance. (See Section 4.6.2.)... 

Opatz and Ferenc [19] produced a small library of 3-amino -(arylamino)-l//-isochromen-l-ones from 2-formylbenzoic acid, potassium cyanide and a series of anilines. The reaction is based on a Strecker mechanism (Scheme 6). 

Figure 8.1 Example structure taken from the PubChem compound database) IUPAC name 4- (2S)-2-acetamido-2-[[(2S)-10-carbamoyl-9-(cyclohexylmethoxy)-2-bicyclo[5.4.0]undeca-7,9,11-trienyl]carbamoyl]ethyl -2-formylbenzoic acid, PubChem CID 9959891.

To synthesize these pharmaceutically interesting compounds, metha-nolic solutions of acetic acid 6 (2.0 eq.)/2-formylbenzoic acid 7 (1.0 eq.) and aniline 8 (2.0 eq.)/potassium cyanide 9 (1.2 eq.) were introduced into the reactor from separate inlets, thus ensuring the formation of HCN and the... 

Formylbenzoic acid, potassium cyanide and anilines react in the presence of acetic acid to afford 3-amino-4-arylamino-isocoumarins (Scheme 215). The reaction proceeds via an initial Strecker reaction to form intermediate 786 followed by intramolecular attack of the carboxyl group onto the nitrile (Scheme 215) <2005EJ0817>. 

C8H603 2-formylbenzoic acid 119-67-5 gas 4.407 1 14903 C8H16 6-methyl-1-heptene 5026-76-6 gas 0.000 2... 

Substituted isocoumarins 27 result from the reaction of 2-iodobenzoic acids with terminal alkynes in ethanol under combined Pd/Cu catalysis <05JOC4778> and a one-pot reaction between 2-formylbenzoic acid, substituted anilines and KCN in AcOH initiated by a Strecker reaction affords good yields of 3-amino-4-(arylamino)isocoumarins (Scheme 10) <05EJO817>. 

Tryptamine, tryptophan and their derivatives are widely used in the synthesis of indolo[3,2,l-naphthyridine derivatives. Thus, refluxing tryptamine 35 with 2-formylbenzoic acid 36 in alcohol followed by the addition of concentrated hydrochloric acid afforded hexahydrobenzo[/z]indolo[3,2,l-[Pg.194]

Employing a stacked-plate micro reactor (channel dimensions = 100 pm, volume = 2 ml), Acke and Stevens [21] investigated the continuous flow synthesis of a series of pharmaceutically relevant chromen-l-ones via the multicomponent route illustrated in Scheme 6.4. To ensure that HCN was formed within the confines of the micro reaction channel, solutions of acetic acid (12) (2 equiv.)-2-formylbenzoic acid (13) (1 equiv.) and aniline (8) (2 equiv.(-potassium cyanide (14) (1.2 equiv.) were introduced into the reactor from separate inlets. A maximum concentration of0.15 M was selected for 13 as this prevented precipitation of the reaction products and intermediates within the micro reactor. Employing a reactant residence time of 40 min, the authors obtained 3-diamino-lff-isochromen-l-one (15) in 66% yield ... 

Naphthalenes have been ozonized in water by at least three groups and the products reported have been rather different. Naphthalene is a particularly active substrate for ozone, kinetically being approximately 1500 times more reactive than benzene (Hoigne and Bader, 1983a) at low pH it is even more reactive than phenol. After application of 2 molar equivalents of ozone, Legube et al. (1986) demonstrated that naphthalene entirely disappeared and that the principal products were phthalic acid (70), 2-formylbenzoic acid (71), hydrogen peroxide, and phthalalde-... 

The one-pot, three-component, highly diastereoselective (95 5 dr) reaction of 2-formylbenzoic acid methyl ester (477) with (5)-(479) and (i )-(480) methylbenzylamine and dimethyl phosphite (478) (the Kabachnik-Fields reaction) proceeded under solvent and catalyst free-conditions to afford the corresponding chiral (3i ,105)-(481a) and (35 ,10i )-(481b) isoindolin-1-one-3-phosphonates in good yields and with high diastereoselectivity (Scheme 119). ... 

Ordonez et al. have developed a practical and efficient strategy to obtain N-substituted dimethyl 3-oxoisoindolin-l-yl phosphonates (241) in a one-pot reaction of 2-formylbenzoic acid, primary amines and dimethyl phosphite. This reaction proceeded in a short time either with conventional heating or microwave irradiation, under catalyst-free conditions, in good yield (69-82%) (Scheme 85). ... 

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