Hydrochloric Acid → 2-Chloro-N-(2,5-dihydroxy-phenyl)-acetamide

HRID 280820Notes

Reaction equation

HRID 280820 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:8]=1[OH:9].N(CCO)CCO.Cl>CC(C)=O.O>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:8]=1[OH:9])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8113DiethanolamineHCID 3017497Aminohydroquinone

Product 1

HCID 212986772-Chloro-N-(2,5-dihydroxy-phenyl)-acetamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

α-chloroacetylchloride (10.1 g, 0.128 mole) was added dropwise under stirring at room temperature to the 2-aminohydroquinone (4.16 g, 0.128 mole) in dry acetone (400 ml) and diethanolamine (2.04 ml, 0.128 mole). The reaction mixture was poured into water and hydrochloride acid (2,000 ml, pH 1), then extracted with ethylacetate (500 ml). The solvent was evaporated to dryness and the solid residue (4.20 g, 80%) was used without any further purification. The structure of the 2-(α-chloroacetamido)-hydroquinone was confirmed by NMR analysis.

Workup

  1. extractionextracted with ethylacetate (500 ml)
  2. customThe solvent was evaporated to dryness
  3. customthe solid residue (4.20 g, 80%) was used without any further purification

Sources & evidence

ORD record
ord-0984854f25914b0bae7e4123b8e452e8
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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