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

HRID 278933Notes

Reaction equation

HRID 278933 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 portionwise 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-6b62f861d3ab4da3b5b53bb49565692a
Source dataset
uspto-grants-2002_03
Patent number
US06362180B1

Reaction notes

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