Sodium Hydroxide → (2-Aminophenyl)(cyclopropyl)methanone

HRID 365970

Reaction equation

HRID 365970 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:14])[CH2:10][CH2:11][CH2:12]Cl.[OH-].[Na+]>C(Cl)Cl.C(Cl)CCl.[Cl-].C[N+](CCCC)(CCCC)CCCC>[CH:10]1([C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[NH2:2])=[O:14])[CH2:12][CH2:11]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 232932461-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride

Product 1

HCID 10931741(2-Aminophenyl)(cyclopropyl)methanoneYield 70%

Reagents, catalysts & solvents 3

HCID 91822Tributylmethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 0.30 g (1.3 mmol) of 1-(o-aminophenyl)-4-chloro-1-butanone hydrochloride in 3 mL of methylene chloride and 3 mL of ethylene dichloride is treated with 1.2 g (3 mmol) of 10% sodium hydroxide solution and 0.05 g (0.2 mmol) of 75% aqueous methyl tributylammonium chloride and heated to 50° C. for about 5 hours. After cooling to room temperature, the phases are separated. The aqueous layer is extracted with methylene chloride. The combined organic extracts are washed with water and concentrated in vacuo to give 0.14 g (70% yield) of o-aminophenyl cyclopropyl ketone (mp 46-48° C.). The product is identified by NMR and MS analyses.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe phases are separated
  3. extractionThe aqueous layer is extracted with methylene chloride
  4. washThe combined organic extracts are washed with water
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1e30ccef6c34666a0b9cc4091476cfe
Source dataset
uspto-grants-2000_10
Patent number
US06127576

Linked notes

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