Sodium Carbonate → N-(1-propyl)-4-hydroxyphenylacetamide

HRID 326562Notes

Reaction equation

HRID 326562 reaction equation
[CH2:1]([NH:4][C:5](=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C(=O)C)=[CH:9][CH:8]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[CH2:1]([NH:4][C:5](=[O:17])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 15730061N-(1-propyl)-4-acetoxyphenylacetamide

Product 1

HCID 10750308N-(1-propyl)-4-hydroxyphenylacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-(1-propyl)-4-acetoxyphenylacetamide (11.4 g) in methanol (25 ml) was added a solution of sodium carbonate (2.65 g) in water (50 ml), and the mixture stirred overnight at ambient temperature. The methanol was removed in vacuo and the aqueous residue acidified to pH2. The product was extracted with ethyl acetate (3×50 ml), and the organic extracts combined and washed with brine (50 ml), dried (MgSO4). The solvent was evaporated to give N-(1-propyl)-4-hydroxyphenylacetamide as a yellow oil, essentially pure by TLC, NMR: 0.85(t,3H, CH3), 1.3-1.6(m,2H, CH2CH3), 3.15(t,2H, CH2N), 3.5(s,2H, CH2Ar), 5.75 (broad t,1H, NH), 6.85(d,2H, phenyl-H), 7.05(d,2H, phenyl-H) (the spectrum also contained peaks due to ethyl acetate); m/e 194 (M+H)+.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionThe product was extracted with ethyl acetate (3×50 ml)
  3. washwashed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5ba1de494b3d440eb1fa3c2e0865d181
Source dataset
uspto-grants-1993_12
Patent number
US05270311

Reaction notes

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