2-Amino-6-chlorobenzoic acid → HCID 136392060, compound

Temperature

50 °C

To a stirred solution of 6-chloro anthranilic acid (6 g, 34.97 mmol) in EtOH (60 mL) under nitrogen atmosphere was added 1.5 equivalent of TEA (14 mL, 104.9 mmol). Upon completion of addition, the mixture was heated to 50° C. where it stirred for 30 min. After this time, a methyl 2,2-diethoxyacetimidate (6 g, 41.96 mmol) in ethanol solution was added through syringe and the resulting mixture was heated to reflux where it stirred for 24 h. At the conclusion of this period, the reaction mixture was cooled to RT and the volatiles were evaporated. The resulting residue was diluted with water, extracted with DCM and washed with brine solution. The crude product was purified by column chromatography (25% ethyl acetate in hexane) to provide 5-chloro-2-(diethoxymethyl)quinazolin-4(3H)-one (7 g, 60% yield). LCMS Method W: retention time 1.5 min; [M+1]=283.

1. additionUpon completion of addition
2. temperaturethe resulting mixture was heated
3. temperatureto reflux where it
4. stirringstirred for 24 h
5. temperatureAt the conclusion of this period, the reaction mixture was cooled to RT
6. customthe volatiles were evaporated
7. additionThe resulting residue was diluted with water
8. extractionextracted with DCM
9. washwashed with brine solution
10. customThe crude product was purified by column chromatography (25% ethyl acetate in hexane)

ORD record

ord-f2cf373738df4782ae499e594452e73f

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575184B2