Isopropanol → 5-Amino-2-chlorophenol

HRID 1252022Notes

Reaction equation

HRID 1252022 reaction equation
[Cl-].[NH4+].C(O)(C)C.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[OH:17]>O>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[C:9]([OH:17])[CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 806765-Amino-2-chlorophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension (about 600 ml) containing 100 g of reduced iron, 5 g of ammonium chloride, 500 ml of isopropyl alcohol, and 100 ml of water was refluxed with vigorous stirring. To this suspension was added 100 g of 2-chloro-5-nitrophenol in portions. After completion of the addition, the mixture was heated for an additional 1 hour. This suspension was filtered when hot with the aid of Celite and the filtrate was washed with about 500 ml of hot isopropyl alcohol and then concentrated to about one-fifth its original volume under reduced pressure. To the concentrate was added 1 l of ice water and the resulting crystalline precipitate was collected by filtration and washed with water.

Workup

  1. temperaturewas refluxed with vigorous stirring
  2. additionAfter completion of the addition
  3. temperaturethe mixture was heated for an additional 1 hour
  4. filtrationThis suspension was filtered when hot with the aid of Celite
  5. washthe filtrate was washed with about 500 ml of hot isopropyl alcohol
  6. concentrationconcentrated to about one-fifth its original volume under reduced pressure
  7. additionTo the concentrate was added 1 l of ice water
  8. filtrationthe resulting crystalline precipitate was collected by filtration
  9. washwashed with water

Sources & evidence

ORD record
ord-2947eb9910634d84b6edc1c976473fca
Source dataset
uspto-grants-1988_05
Patent number
US04741997

Reaction notes

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