Hydrochloric Acid → 1-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride

HRID 365969

Reaction equation

HRID 365969 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[CH2:9][CH2:10][CH2:11]O.[ClH:14]>O>[ClH:14].[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[CH2:9][CH2:10][CH2:11][Cl:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 112061181-(o-Aminophenyl)-4-hydroxy-1-butanone

Product 1

HCID 232932461-(o-Aminophenyl)-4-chloro-1-butanone hydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.3 g (5.1 mmol) of 1-(o-aminophenyl)-4-hydroxy-1-butanone, 26 mL of water and 90 mL of 37% HCl is refluxed for about 6.5 hours, cooled and filtered to afford 8.0 g of 1-(o-aminophenyl)-4-chloro-1-butanone hydrochloride. Extraction of the aqueous mother liquor with methylene chloride gives an additional 1.10 g of the title product for an overall yield of 73% (mp 142-145° C.). The product is identified by NMR and MS analyses.

Workup

  1. temperatureis refluxed for about 6.5 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b8b11781c5314a5195fcb3226aa20638
Source dataset
uspto-grants-2000_10
Patent number
US06127576

Linked notes

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