Hydrochloric Acid → 2-Amino-4-chloro-5-methylphenol

HRID 337366

Reaction equation

HRID 337366 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.Cl.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:10][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([CH3:8])=[CH:6][C:5]=1[OH:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 235324-Chloro-5-methyl-2-nitrophenolHCID 25517Ammonium Chloride

Product 1

HCID 1045242-Amino-4-chloro-5-methylphenolYield 33.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g).

Workup

  1. filtrationThen the insoluble material was filtered off through celite
  2. washthe celite cake was washed with ethyl acetate (100 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-97d8b1235d82491fa0de0d796401146c
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Linked notes

Loading…