5-Chlorovaleryl chloride → 1-(4-Acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one

HRID 963339

Reaction equation

HRID 963339 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:6]=1[Cl:13])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)CCl>[C:1]([NH:4][C:5]1[C:6]([Cl:13])=[CH:7][C:8]([C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][Cl:18])=[C:9]([OH:11])[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 19081918N-(2-Chloro-5-methoxyphenyl)acetamide

Product 1

HCID 190818791-(4-Acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-oneYield 70.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-Acetyl-2-chloro-5-methoxyaniline (10.0 g, 50 mmol), aluminum chloride (13.3 g, 100 mmol), and 5-chloropentanoyl chloride (11.7 g, 75 mmol) were combined in ethylene dichloride (100 mL) and the mixture was stirred at room temperature and under nitrogen for 7 days. The mixture was then poured onto crushed ice and extracted into methylene chloride. The methylene chloride extract was washed with water and then dried. The solvent was evaporated in vacuo. Crystallization of the residue from ethyl acetate/hexane gave 1-(4-acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one (10.18 g, 35.1 mmol), m.p. 126°-128° C.

Workup

  1. additionThe mixture was then poured
  2. customonto crushed ice
  3. extractionextracted into methylene chloride
  4. extractionThe methylene chloride extract
  5. washwas washed with water
  6. customdried
  7. customThe solvent was evaporated in vacuo
  8. customCrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1949f987f8d045ae9e573ed8d6558f1a
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Linked notes

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