Methyl 3-aminophenylacetate → 3-(Methylthio)phenylacetic acid

HRID 2289230Notes

Reaction equation

HRID 2289230 reaction equation
N[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11]C)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][S-:14].[K+]>>[CH3:13][S:14][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 13054266Methyl 3-aminophenylacetateHCID 23693077Potassium Methanethiolate

Product 1

HCID 27374613-(Methylthio)phenylacetic acidYield 17.2%

Procedure

Prepared in an essentially similar fashion from methyl 3-aminophenylacetate (111 g, 0.67 mole) and potassium methanethiolate (2.68 mole) to give 3-methylthiophenylacetic acid (21.0 g). Mp=76-77° C., 1H NMR (DMSO-d6, 200 MHz) δ: 2.44 (s, 3H, SCH3), 3.53 (s, 2H, ArCH2) 7.02-7.28 (m, 4H, Ar), 12.30 (br s, 1H, CO2H). Mass spectrum (CI--CH4): 183 (M+1, 100%). (Lit. ref.: Plant Physiol 42(11) 2596-1600 (1967).

Sources & evidence

ORD record
ord-7825dc2549824d18a3f9d765a89ee6e4
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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