Water → N-(2-chloro-4-hydroxyphenyl)acetamide

HRID 478323Notes

Reaction equation

HRID 478323 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[Cl:10].[C:11]([O-])(=[O:13])[CH3:12].[Na+].O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C:11]([NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[Cl:10])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 125981904-Amino-3-chlorophenol hydrochloride

Product 1

HCID 14590937N-(2-chloro-4-hydroxyphenyl)acetamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Part E. A solution of 4-amino-3-chlorophenol hydrochloride (18.6 g, 103 mmol) and sodium acetate (18.6 g, 227 mmol) in glacial acetic acid (200 mL) was heated to gentle reflux for 12 hours, then cooled and poured into 4 volumes water. This was neutralized with portion wise addition of sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate (2×500 mL). The extracts were washed with brine, combined, dried over magnesium sulfate, filtered and evaporated. The resulting solid was triturated with warm ether; filtration and vacuum drying gave 4-acetamido-3-chlorophenol (16.1 g, 86.7 mmol, 84%). m.p. 128-129° C. TLC RF 0.14 (50:50 ethyl acetate-hexane). 1H NMR (300 MHz, 4:1 CDCl3.CD3OD): d 7.66 (1H, d, J=8.8 Hz), 6.88 (1H, d, J=1.7 Hz), 6.74 (1H, dd, J=8.8, 1.7 Hz), 2.19 (3H, s). MS (H2O-GC/MS): m/e 186 (100).

Workup

  1. temperatureto gentle reflux for 12 hours
  2. temperaturecooled
  3. extractionthe resulting mixture was extracted with ethyl acetate (2×500 mL)
  4. washThe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was triturated with warm ether
  9. filtrationfiltration and vacuum
  10. customdrying

Sources & evidence

ORD record
ord-cb20c37132ff45bf94c9e89b401fbb42
Source dataset
uspto-grants-2003_11
Patent number
US06642230B2

Reaction notes

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