Methyl p-aminosalicylate → HCID 18961218, compound

HRID 1708220Notes

Reaction equation

HRID 1708220 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]([OH:30])[C:23](=[CH:28][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25]>>[OH:30][C:22]1[CH:21]=[C:20]([NH:19][C:14]([C:8]2[S:7][C:6]3[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[C:9]=2[O:10][CH:11]([CH3:12])[CH3:13])=[O:16])[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

3

Reactant 2

HCID 77787Methyl p-aminosalicylateHCID 139616485-Methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 18961218HCID 18961218, compoundYield 59.1%

Procedure

Following a procedure analogous to Example 12, 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid (200 mg, 0.75 mmol) and methyl 4-aminosalicylate (117 mg, 0.70 mmol) [obtained by esterification of 4-aminosalicylic acid, sodium salt (Sigma) with iodomethane] provides 172 mg (59%) of product; mp 158.5°-160° C.

Sources & evidence

ORD record
ord-03ab4ac33ba243e98054c2cc57251343
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

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