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

HRID 1596506Notes

Reaction equation

HRID 1596506 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-methylacetamide

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) and stirred overnight at room temperature. Methanol was then displaced under vacuum with ethyl acetate. The resulting slurry (ca. 20 gal) was stirred at +10° C. for 1 hour, then filtered and dried under vacuum at 45° C. to yield of the title compound(18.68 kg, 94% of theory). mp 124-125° C. NMR (300 MHz, d6-DMSO): δ=9.26 (s, 1H), 8.00-7.65 (br s, 1H), 7.21-6.90 (m, 2H), 6.86-6.55 (m, 2H), 3.26 (s, 2H), 2.75-2.45 (m, 3H).

Workup

  1. stirringThe resulting slurry (ca. 20 gal) was stirred at +10° C. for 1 hour
  2. filtrationfiltered
  3. dry with materialdried under vacuum at 45° C. to yield of the title compound(18.68 kg, 94% of theory)

Sources & evidence

ORD record
ord-b4ade44cb80b44759370ee17a4128984
Source dataset
uspto-grants-2001_09
Patent number
US06291489B1

Reaction notes

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