Methylamine → 2-(4-Hydroxyphenyl)-N-methylacetamide

HRID 431270Notes

Reaction equation

HRID 431270 reaction equation
[CH3:1][NH2:2].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C(OCC)(=O)C>CO>[CH3:1][NH:2][C:5](=[O:4])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 129230782-(4-Hydroxyphenyl)-N-methylacetamideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Monomethylamine, (22.43 kg, 722.15 mol, 6 eq.) was added over a 7-hour period to a solution of methyl-4-hydroxyphenylacetate (20.0 kg, 120.35 mol, 1.0 eq.) in methanol (31.7 gal, 120 L) and stirred overnight at room temperature. Methanol was then displaced under vacuum with ethyl acetate. The resulting slurry (about 20 gal, 75.7 L) was stirred at +10° C. for 1 hour, then filtered and dred under vacuum at 45° C. to yield the title compound(18.68 kg, 94% of theory).

Workup

  1. stirringThe resulting slurry (about 20 gal, 75.7 L) was stirred at +10° C. for 1 hour
  2. filtrationfiltered
  3. customdred under vacuum at 45° C.

Sources & evidence

ORD record
ord-c397e973ce45467b90862553defb16ec
Source dataset
uspto-grants-2003_12
Patent number
US06657063B1

Reaction notes

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