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

HRID 1856675Notes

Reaction equation

HRID 1856675 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 m z 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-a38bb51c8075404aabca22e3022734c4
Source dataset
uspto-grants-2000_11
Patent number
US06143743

Reaction notes

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