Pyridine → Methyl 4-amino-3-[(4-tert-butylbenzoyl)amino]benzoate

To a stirring solution of 4-methoxycarbonyl-1,2-benzenediamine (8.5 g, 51 mmol) and pyridine (4.1 mL, 51 mmol) in acetonitrile (225 mL) at 0° C. was added via an addition funnel a solution of 4-t-butylbenzoyl chloride (10 g, 51 mmol) in acetonitrile (25 mL). After 3 h, the mixture was concentrated to a volume of about 20 mL in vacuo and then diluted with ethyl acetate (300 mL) and water (100 mL). The phases were separated and the organic phase was washed twice with 1 M citric acid, once with brine, twice with satd aq NaHCO3 and once again with brine. The organic phase was then dried with MgSO4, filtered and partially concentrated in vacuo. After standing for 48 h, the resulting precipitate was filtered, washed with ethyl acetate and dried in vacuo to give 8.2 g (48%) of off white solid. By a similar procedure, a second crop of 2.6 g (16%) was isolated from the mother liquor.

1. concentrationthe mixture was concentrated to a volume of about 20 mL in vacuo
2. additiondiluted with ethyl acetate (300 mL) and water (100 mL)
3. customThe phases were separated
4. washthe organic phase was washed twice with 1 M citric acid, once with brine, twice with satd aq NaHCO3 and once again with brine
5. dry with materialThe organic phase was then dried with MgSO4
6. filtrationfiltered
7. concentrationpartially concentrated in vacuo
8. waitAfter standing for 48 h
9. filtrationthe resulting precipitate was filtered
10. washwashed with ethyl acetate
11. customdried in vacuo
12. customto give 8.2 g (48%) of off white solid
13. customBy a similar procedure, a second crop of 2.6 g (16%) was isolated from the mother liquor

ORD record

ord-8bc9dfa9897d4b3887d0f04c4a65757b

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06372759B1