Hydrochloric Acid → 1-(4-Amino-2-hydroxy-3-methyl-phenyl)-ethanone

HRID 1818474Notes

Reaction equation

HRID 1818474 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].O.Cl>CCO.[Fe]>[NH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 153725201-(2-Hydroxy-3-methyl-4-nitro-phenyl)-ethanone

Product 1

HCID 574383081-(4-Amino-2-hydroxy-3-methyl-phenyl)-ethanoneYield 74.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1-(2-hydroxy-3-methyl-4-nitro-phenyl)-ethanone (720 mg, 3.7 mmol) in EtOH (30 mL) are consecutively added Fe powder (4 g, 74 mmol), water (7.2 mL), and conc. HCl (145 μL). The reaction mixture is heated at 95° C. for 4 h. The iron is filtered through celite and the filtrate poured slowly into saturated aqueous NaHCO3. After the bubbling subsides, the mixture is extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried over Na2SO4, and concentrated. The residue is purified by 25% EtOAc/hexane. Obtained is the title compound as a white solid (455 mg). LC-MS (m/e): 166 (M+1).

Workup

  1. filtrationThe iron is filtered through celite
  2. additionthe filtrate poured slowly into saturated aqueous NaHCO3
  3. extractionAfter the bubbling subsides, the mixture is extracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue is purified by 25% EtOAc/hexane
  8. customObtained

Sources & evidence

ORD record
ord-bb578899b50c4b33820ed6366da858e7
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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