Ammonium Chloride → 5-Benzyloxy 1-para-aminophenyl 1-pentanone

HRID 462720Notes

Reaction equation

HRID 462720 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>[Fe].C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 132730465-Benzyloxy 1-para-nitrophenyl 1-pentanone

Product 1

HCID 132730475-Benzyloxy 1-para-aminophenyl 1-pentanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 23 g of formula (IX) compound obtained in the preceding example and 23 g of powdered iron in 200 ml of an aqueous solution of 10% ammonium chloride and 20 ml of ethanol was left under agitation for an hour at room temperature. Then it was extracted with methylene chloride, filtered, the filtrate was washed with water, dried on sodium sulfate, filtered, the filtrate was evaporated and the residue crystallized in a mixture of ethyl acetate and isopropylic ether. 18.6 g of the expected compound were obtained.

Workup

  1. waitwas left under agitation for an hour at room temperature
  2. extractionThen it was extracted with methylene chloride
  3. filtrationfiltered
  4. washthe filtrate was washed with water
  5. customdried on sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customthe residue crystallized in a mixture of ethyl acetate and isopropylic ether

Sources & evidence

ORD record
ord-85922ff6c0a746a3b35fa11c48dc64ca
Source dataset
uspto-grants-1985_05
Patent number
US04517197

Reaction notes

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