Methyl 4-amino-3-methoxybenzoate → 2486-69-3

HRID 1708219Notes

Reaction equation

HRID 1708219 reaction equation
COC1C=CC2SC(C(O)=O)=C(OC(C)C)C=2C=1.[NH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][C:21]=1[O:30][CH3:31]>CO>[NH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 602411Methyl 4-amino-3-methoxybenzoateHCID 139616485-Methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 2880572486-69-3

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure analogous to Example 12, 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid (230 mg, 0.86 mmol) and methyl 4-amino-3-methoxybenzoate (310 mg, 1.38 mM) [obtained by esterification of 4-amino-3-methoxybenzoic acid (Aldrich) with MeOH/AcC1]provides 269 mg (73%) of product; mp 278° C. dec. Saponification of 100 mg of methyl 3-methoxy-4-[[[5-methoxy-3-(1-methylethoxy)benzo [b]thien-2-yl]carbonyl]amino]benzoate gives 48 mg (50%) of product; mp 278°-281° C. dec.

Sources & evidence

ORD record
ord-31d8e7b812504d54a7c2898cc51ba360
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

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