4-Chloroaniline → HCID 23141392, compound

Temperature

0 °C

5-(Methoxycarbonyl)-2-nitrobenzoic acid (CAS registry number: 76143-33-4) (1.50 g) and 0.05 mL of N,N-dimethylformamide were dissolved in 150 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 0.87 mL of oxalyl chloride was added little by little, and the mixture was stirred for 30 minutes at 0° C., followed by stirring the mixture for 13 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid, which was dissolved in 150 mL of dichloromethane. To this solution, a solution of 0.94 g of 4-chloroaniline and 3.57 mL of N,N-diisopropylethylamine dissolved in 25 mL of dichloromethane was added little by little. The mixture was stirred for 2 hours and a half at room temperature, whereafter 100 mL of a saturated aqueous solution of ammonium chloride was added to separate the organic layer. The aqueous layer was extracted twice with 50 mL of dichloromethane. The respective organic layers were combined, whereafter the combined organic layer was washed with 50 mL of a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and washed with dichloromethane. The filtrate and the washings were combined, and dichloromethane was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography. The resulting solid was dried under reduced pressure to obtain 1.82 g (81%) of methyl N-(4-chlorophenyl)-4-nitroisophthalamate.

1. stirringby stirring the mixture for 13 hours at room temperature
2. distillationThe reaction mixture was distilled under reduced pressure
3. customdried
4. customto obtain a light yellow solid, which
5. additionwas added little by little
6. stirringThe mixture was stirred for 2 hours
7. customto separate the organic layer
8. extractionThe aqueous layer was extracted twice with 50 mL of dichloromethane
9. washwas washed with 50 mL of a saturated aqueous solution of sodium chloride
10. dry with materialdried over anhydrous sodium sulfate
11. customThe anhydrous sodium sulfate was separated by filtration
12. washwashed with dichloromethane
13. distillationdichloromethane was distilled off under reduced pressure
14. customThe resulting residue was purified by silica gel column chromatography
15. customThe resulting solid was dried under reduced pressure

ORD record

ord-f1643bf39f2b47ab9c858e4e14a3e2cb

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063046B2