Dimethylformamide → 2-(3-Nitro-6-methoxy-2-pyridinylamino)-3,3-diphenylpropionic acid

HRID 2305373Notes

Reaction equation

[NH2:1][CH:2]([CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22]([O:29][CH3:30])[N:21]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O.C(OCC)(=O)C>[N+:26]([C:25]1[C:20]([NH:1][CH:2]([CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([OH:5])=[O:4])=[N:21][C:22]([O:29][CH3:30])=[CH:23][CH:24]=1)([O-:28])=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

2.50 g (10.4 mmol) of 2-amino-3,3-diphenylpropionic acid, 0.84 g (4.3 mmol) of 2-chloro-3-nitro-6-methoxypyridine and 0.55 g (5.2 mmol) of sodium carbonate were introduced into 18 ml of DMF and 18 ml of water, and the mixture was stirred at 80° C. for 5 hours. Ethyl acetate and water were then added, and the phases were separated. The aqueous phase was acidified with 6 normal hydrochloric acid and extracted three times with ethyl acetate. After drying with MgSO4 and concentration under reduced pressure, the crude product was recrystallized from isopropanol. 0.34 g (20.1%) of a yellow powder of melting point 172-180° C. was obtained.

Workup

customthe phases were separated
extractionextracted three times with ethyl acetate
dry with materialAfter drying with MgSO4 and concentration under reduced pressure
customthe crude product was recrystallized from isopropanol

Sources & evidence

ORD record: ord-1cbc4c87130a4ff3ac903c26a9909762
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06440975B1

Reaction notes

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