Sodium Methoxide → Acrylanilide, 4'-hydroxy-

HRID 1970755Notes

Reaction equation

HRID 1970755 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C(=O)C)=[CH:8][CH:7]=1)(=[O:4])[CH:2]=[CH2:3].C[O-].[Na+]>CO>[OH:12][C:9]1[CH:8]=[CH:7][C:6]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69041419Acetic acid 4-acryloylamino-phenyl ester

Product 1

HCID 36830Acrylanilide, 4'-hydroxy-Yield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 2 (200 mg, 0.98 mmol) in 1.5 ml of MeOH in a 5 ml screw-capped vial is added 1.0 ml of 0.5 M of sodium methoxide in MeOH. The mixture is stirred at ambient temperature, and the reaction is complete in 10 min. The mixture is neutralized by addition of cation exchange resin (Dowex, 50W×8, H+) (moist pH paper). The resin is removed by filtration and washed with MeOH. The combined filtrate and wash is concentrated by rotary evaporation to yield an off-white solid (152 mg, 95%), ESI-MS (M+H)+: 164.2. 1H-NMR (acetone-d6), δ 9.15 (1H, br, NH), 7.59 (2H, d, J=9.0 Hz, NHCCH), 6.82 (2H, d, J=9.0 Hz, NHCCHCH), 6.52˜6.35 (2H, m, COCHCHH (anti to each other)), 5.70 (1H, dd, J=9.8 and 2.2 Hz, COCHCHH (syn to COCH)).

Workup

  1. customThe resin is removed by filtration
  2. washwashed with MeOH
  3. washThe combined filtrate and wash
  4. concentrationis concentrated by rotary evaporation

Sources & evidence

ORD record
ord-586eaa486abf40e89b80cf7996712e57
Source dataset
uspto-grants-2013_04
Patent number
US08431335B2

Reaction notes

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