Ethyl 3-aminobenzoate → 3-[[[5-Methoxy-3-(1-methylethoxy)benzo[b]thien-2-yl]carbonyl]amino]benzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]([C:14]([OH:16])=O)=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]=2[CH:4]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([O:25]CC)=[O:24]>>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]([C:14]([NH:19][C:20]3[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=3)[C:23]([OH:25])=[O:24])=[O:16])=[C:9]([O:10][CH:11]([CH3:12])[CH3:13])[C:5]=2[CH:4]=1Participants
3
Procedure
Following a procedure analogous to Example 12, 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid (7.0 g, 26 mmol) and ethyl 3-aminobenzoate (4.3 g, 26 mmol) provides 8.5 g (78%) of the intermediate ester. Saponification of the crude ester followed by recrystallization from aqueous ethanol gives 4.2 g (53%) of product; mp 197°-200° C. (dec).
Sources & evidence
- ORD record
- ord-e5d30fca22c245ea8a0767555b56a2ce