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

HRID 1708002Notes

Reaction equation

HRID 1708002 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-b3e2cc64ba2146648c2f330fa53888b2
Source dataset
uspto-grants-1994_10
Patent number
US05356894

Reaction notes

Loading…