HCID 22290987, compound → HCID 22290997, compound

Temperature

-5 °C

A suspension of 2-acetylamino-4-methoxy-benzoic acid (15 g, 73.7 mmol) in water (75 mL) was cooled to −5° C. and conc HCl (150 mL) was added followed by cooling to −5°. To this mixture was added a solution of NaNO2 (5.43 g, 77.4 mmol) in water (50 mL) that had been cooled to −5°; this solution was added at such a rate so as to maintain the temperature of the reaction mixture between −5° and 0° C. The reaction mixture was stirred for 10 min and the clear solution was added to a solution of stannous chloride (41.9 g, 221 mmol) in conc HCl (150 mL) that had been cooled to −20° C. This addition was conducted so as to maintain a temperature of −20° to −10° C. for the reaction mixture, followed by stirring the mixture for 1.5 h at −20° C. The solid that formed was collected by filtration, washed with chilled EtOH, and dried to give an off-white solid (10.8 g): APCl/LCMS m/z 183 (M+H)+.

1. temperatureby cooling to −5°
2. temperaturehad been cooled to −5°
3. additionthis solution was added at such a rate so as
4. temperatureto maintain the temperature of the reaction mixture between −5° and 0° C
5. temperaturehad been cooled to −20° C
6. additionThis addition
7. temperatureto maintain a temperature of −20° to −10° C. for the reaction mixture
8. stirringby stirring the mixture for 1.5 h at −20° C
9. customThe solid that formed
10. filtrationwas collected by filtration
11. washwashed with chilled EtOH
12. customdried

ORD record

ord-fba75b8ed3b447e4beac587b1a4a445f

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06956036B1