3- Chloropropanoyl chloride

Performing a Vilsmeier-Haack reaction on 3-benzoyloxy-2-methyl-quinazolin-4-one (184) afforded the isoxazolo[3,2- ]quinazolinone (185) [86IJC(B)709]. This ring system (187) was also synthesized by cyclocondensation of anthranilic acids or isatoic anhydrides with the isoxazolin-3-ones (186) (77AF766 83MIP1), or by condensation of methyl anthrani-late with 3-chloropropanoyl chloride followed by cyclization with hydroxylamine hydrochloride (77AF766). 

Figure 5.26 summarizes our synthesis of 141. Friedel-Crafts acylation of neat A with 3-chloropropanoyl chloride and boron trifluoride etherate gave B. Ring closure of B to C was effected with potassium carbonate in ethanol. Then, C was converted to 1,3-benzodioxole E via D. The reason for this conversion was to make later deprotection easy. 

The preparafion of 5-chloroindanone 55, useful in the production of agrochemicals, can be simply performed in 75% yield by elecfrophilic cyclo(acylation-alkylafion) of chlorobenzene wifh 3-chloropropanoyl chloride in the presence of an excess of hydrofluoric acid and a stoichiometric amount of boron frifluoride wifhouf solvenf (Scheme 2.24). ... 

Reactions of Miscellaneous Haloketones - Acetyl chloride undergoes photochemical loss of HCl when irradiated either neat or in a matrix.Irradiation of 3-chloropropanoyl chloride in a matrix using wavelengths greater than 230 nm yields 3-chloro-l,2-propenone and acryloyl chloride as the principal photochemical products. ... 

Diaza-compounds. The pyrrolo-pyrazole derivative (705) is one of the products of the action of acids on the tosylhydrazone H2C=CMe(CH2)2CH=N—NHTos. The reaction of 2,5,5-trimethyl-l-pyr-roline iV-oxide (706) with the ketenimine Ph2C=C=NPh yields the pyrrolo-imidazole (707)/ Pyrazolidin-3-one and 3-chloropropanoyl chloride combine to form the dioxopyrazolopyrazole (708)/ Irradiation of l-(o-iodoben-zoyl)imidazole (709 R=H) produces the indolobenzimidazolinone (710) the... 

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