3'-Nitro-4'-methylacetophenone → 1-(3-Amino-4-methylphenyl)ethan-1-ol

HRID 1019075Notes

Reaction equation

HRID 1019075 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-])=O.[BH4-].[Na+].[H][H]>CO.C(OCC)(=O)C.[Pd]>[OH:9][CH:8]([C:5]1[CH:4]=[C:3]([C:2]([CH3:1])=[CH:7][CH:6]=1)[NH2:11])[CH3:10]

Participants

7

Reactant 3

HCID 792463'-Nitro-4'-methylacetophenoneHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 120512021-(3-Amino-4-methylphenyl)ethan-1-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cold solution of 4-methyl-3-nitroacetophenone (25 g, 139 mmol) in methanol (200 mL) is added sodium borohydride (6.2 g, 163 mmol) over 15 minutes. The mixture is stirred at room temperature for 1 hour, then is quenched with water. The mixture is rotary evaporated and the residue is partitioned between water and ethyl acetate. The organic layer is dried (magnesium sulfate) and rotary evaporated to afford a light brown viscous oil. The oil is diluted with ethyl acetate (200 mL), 5% palladium-on-carbon (5 g) is added and the mixture is treated with hydrogen at 40 psi for 18 hours. The mixture is then filtered on Celite and the filtrate is rotary evaporated to afford 3-(1-hydroxyethyl)-6-methylaniline as a light yellow, pasty solid.

Workup

  1. customis quenched with water
  2. customThe mixture is rotary evaporated
  3. customthe residue is partitioned between water and ethyl acetate
  4. dry with materialThe organic layer is dried (magnesium sulfate)
  5. customrotary evaporated
  6. customto afford a light brown viscous oil
  7. additionis added
  8. filtrationThe mixture is then filtered on Celite
  9. customthe filtrate is rotary evaporated

Sources & evidence

ORD record
ord-d55df7e059594cfc98560ab9442fa27c
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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