Methylamine → methoxy-N-methylphenylacetamide

HRID 617400Notes

Reaction equation

HRID 617400 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][O:7][C:6]1=[O:15]>CO>[OH:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH:5]([O:4][CH3:3])[C:6]([NH:2][CH3:1])=[O:15].[CH3:3][O:4][CH:5]([C:14]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:6]([NH:2][CH3:1])=[O:7]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 155472854-Methoxy-3-isochromanone

Product 2

HCID 15642519methoxy-N-methylphenylacetamideYield 96.5%HCID 702393162-hydroxymethyl-alpha-methoxy-N-methyl-phenylacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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-methylphenyl-acetamide (8.50 g, 96.5%) as white crystals.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5e57fcad33804ae29438ebb077638b22
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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