4-Methoxy-3-isochromanone → methoxy-N-methylphenylacetamide

HRID 428002Notes

Reaction equation

HRID 428002 reaction equation
[CH3:1][NH2:2].CO.[CH3:5][O:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][O:9][C:8]1=[O:17]>CO>[OH:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1[CH:7]([O:6][CH3:5])[C:8]([NH:2][CH3:1])=[O:17].[CH3:5][O:6][CH:7]([C:16]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]([NH:2][CH3:1])=[O:9]

Participants

5

Reactant 2

HCID 155472854-Methoxy-3-isochromanoneHCID 57454252Monomethylamine methanol

Product 2

HCID 15642519methoxy-N-methylphenylacetamideYield 225.3%HCID 702393162-hydroxymethyl-alpha-methoxy-N-methyl-phenylacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40% methylamine-methanol solution (9.80 g, 126 mmol) was added to 4-methoxy-3-isochromanone (7.50 g, 42.1 mmol) in methanol (40 ml), and the mixture was stirred at room temperature for 1 hour. Evaporation of the solvent gave the desired compound 2-hydroxymethyl-(α-methoxy-N-methylphenylacetamide (8.50 g, 96.5%) as white crystals.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8561b449f34d42128ad6031dda5ace2a
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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