Methyl ester nitrous acid

Methyl ester nitrous acid H2NCH2-C(0)0H 83.1+2.5 347.7+10.5 Derived from in ref. 1996NIST... 

Methyl nitrite Nitrous acid, methyl ester (8,9) (624-91-9) Acetonitrile, 2-tgrt-butoxycarbonyloxyimino-2-phenyl- (8) Benzeneacetonitrile, a -[[[(1, l-dimethylethoxy)carbonyl]oxy]imino]-(9) (58632-95-4)... 

SYNS NITROUS ACID-sec-BUTYL ESTER NITROUS ACID-1-METHYL PROPYL ESTER... 

The butyric acid derivative (19) has been synthesized by thermal rearrangement of the isoxazolidine (18) obtained by 1,3-dipolar addition of a nitronic ester to methyl acrylate. Nitrous acid deamination of (25,35)-isoleucine has been found to give predominantly (95 %) (25, 35)-2-hydroxy-3-methylvaleric acid (20). 

Indazoles can be considered as either azaindoles or azaisoindoles depending on the reader s prejudice. Benzydamine (54) represents a drug with this heterocyclic nucleus. Alkylation of the amine of anthranilic acid methyl ester with benzyl chloride in the presence of sodium acetate gives 52. Treatment with nitrous acid leads to the nitrosoamine, which cyclizes spontaneously to the 3-ketoindazole system, 53. This intermediate forms an ether of its enol form on heating the sodium salt with 3-dimethylaminopropyl chloride. There is thus obtained benzydamine (54), a fairly potent nonsteroidal antiinflammatory agent with significant antipyretic and analgesic properties. 

Deamination of the methyl ester (19) of 2-amino-2-deoxy-L-gluconic acid with nitrous acid gave methyl 2,5-anhydro-L-... 

Isocarboxazid Isocarboxazid, 2-benzylhydrazid-5-methyl-3-isoxazolecarboxylate (7.2.6), can be synthesized from acetylacetone, which on nitrosation with nitrous acid gives 5-methyl-isoxazol-3-carboxyhc acid (7.2.2). Esterification of this product gives the ethyl ester of 5-methyl-isoxazol-3-carboxyhc acid (7.2.3). The synthesized ester (7.2.3) is further reacted with benzylhydrazine, to give isocarboxazide (7.2.6), or with hydrazine, which forms 5-methyl-isoxazol-3-carboxylic acid hydrazide (7.2.4). Reacting the latter with benzaldehyde gives hydrazone (7.2.5), which is further reduced to the isocarboxazide (7.2.6) [46,47]. 

The best known example of the treatment of a primary aliphatic amine with nitrous acid involves the reaction of esters of glycine hydrochloride with sodium nitrite to form esters of diazoacetic acid. This reaction is carried out at low temperatures and under such reaction conditions that any IV-nitroso primary amine which might have been formed is immediately converted to the diazoacetate [15, 16]. Treatment of 1-methyl-2,2,2-trifluoroethylamine hydrochloride, another primary amine, with sodium nitrite in an aqueous system also evidently leads to the corresponding diazoalkane [17]. 

The original method of preparing diazomethane is as follows. Methyl-urethane, formed by the interaction of methylamine and chloroformic ester, is converted into the nitroso compound by the action of nitrous acid, the latter yielding diazomethane on treatment with alcoholic potash. 

In 1989, a different approach was published by Orito [60], in which elaidinization ((Z) —> ( ) double bond isomerization) is used to obtain ( )-MNA from a (Z, )-mixture ofdiastereomers (Scheme 4.6). Gannet had observed that the iodine-induced photoisomerization of the methyl ester of MNA (48) gave only a 7 3 ( /Z) mixture [59], but Orito obtained a better diastereomeric ratio (8 1) using nitrous acid. Remarkably, no double-bond migration to form the more stable trisubstituted olefin was observed. This discovery paved the way to a very simple and general synthesis of the acidic component of capsaicinoids. Thus, a Wittig reaction of the phosphonium salt of a 6-bromohexanoic acid (49) with isobutyraldehyde (SO) afforded a 1 11... 

SYNS ISOAMYL NITRITE ISOPENTYX ALCOHOL NITRITE 3-METHYLBUTANOL NITRITE 3-METHYLBUTVL NITRITE NITROUS ACID-3-METHYL BUTYL ESTER VAPOROLE... 

NITROUS ACID-n-BUTYL ESTER see BRV500 NITROUS ACID-sec-BUTYL ESTER see BRV750 NITROUS ACID, ISOBUTYL ESTER see IJDOOO NITROUS ACID-3-METHYL BUTYL ESTER see IMBOOO NITROUS ACID, METHYL ESTER see MMF750 NITROUS ACID, 1-METHYLETHYI. ESTER (9CI) see IQQOOO... 

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