HCID 14275604, compound → 2,5-Dimethyl-6-chloro-4-aminophenol

HRID 569730Notes

Reaction equation

HRID 569730 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[C:4]([Cl:12])[C:3]=1[OH:13]>C(O)C.[Pt]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:11])=[C:4]([Cl:12])[C:3]=1[OH:13]

Participants

4

Reactant 1

HCID 14275604HCID 14275604, compound

Product 1

HCID 142756052,5-Dimethyl-6-chloro-4-aminophenolYield 96.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Into a Parr bottle containing 5.0 grams (24.8 mmol) of 2,5-dimethyl-6-chloro-4-nitrophenol in 40 milliliters of ethyl alcohol was added 0.5 grams of 5 percent platinum on carbon. This mixture was hydrogenated for 45 minutes in a Parr apparatus. The resulting solution was filtered over charcoal and Celite and the solvent was evaporated to afford 4.09 grams of 2,5-dimethyl-6-chloro-4-aminophenol having a melting point of 127° C.-128° C. Recrystallization from ethyl acetate and hexane afforded a product having a melting point of 129° C.-130° C. Elemental analysis of the product indicated the following:

Workup

  1. filtrationThe resulting solution was filtered over charcoal and Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e9db3238bdee453e89c15455b9e08ecc
Source dataset
uspto-grants-1988_03
Patent number
US04734404

Reaction notes

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