Hydrochloric Acid → 2-Amino-4-methoxyphenol hydrochloride

HRID 2114401Notes

Reaction equation

HRID 2114401 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1.[ClH:13]>[Pd].C(OCC)(=O)C>[NH2:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[OH:9].[ClH:13].[NH2:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15285Phenol, 4-methoxy-2-nitro-

Product 2

HCID 14191082-Amino-4-methoxyphenolHCID 30156182-Amino-4-methoxyphenol hydrochlorideYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 1 L round bottom 3-neck flask equipped with a magnetic stir bar was charged with 4-methoxy-2-nitrophenol (10.0 g, 59.0 mmol) and 10% Pd/C (1 g, 10% by weight) under argon. Ethyl acetate (200 mL) was then added very slowly to the mixture under argon. The mixture was stirred vigorously at room temperature for several minutes before 1.8 mL of concentrated hydrochoric acid was added. The argon was evacuated from the flask under reduced pressure and the flask was then charged with 1 atm of hydrogen gas and stirred for 18 hours at room temperature before its progress was checked by HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid). The chromatogram indicated that all of the starting material (Rt=5.9 min) was consumed and a new single peak had formed (Rt=2.3 min). The reaction was filtered through 10 g plug of Celite. The organic filtrate was then concentrated by rotary evaporation to give 2-amino-4-(methyloxy)phenol as the HCl salt (6.62 g, 38 mmol, 64%) in the form of a brown amorphous solid. MS (ES) m/e 140 [M+H]+.

Workup

  1. customA 1 L round bottom 3-neck flask equipped with a magnetic stir bar
  2. additionwas added
  3. customThe argon was evacuated from the flask under reduced pressure
  4. additionthe flask was then charged with 1 atm of hydrogen gas
  5. customwas consumed
  6. customa new single peak had formed (Rt=2.3 min)
  7. filtrationThe reaction was filtered through 10 g plug of Celite
  8. concentrationThe organic filtrate was then concentrated by rotary evaporation

Sources & evidence

ORD record
ord-6bb1a5e3217947e88dc93cfafd303290
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

Loading…