Sodium borohydride → 3-Benzyloxy-4-methyl-phenylamine

HRID 395758

Reaction equation

HRID 395758 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.CO.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[CH3:15])[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 181745022-Benzyloxy-1-methyl-4-nitro-benzene

Product 1

HCID 27946253-Benzyloxy-4-methyl-phenylamineYield 97%

Reagents, catalysts & solvents 3

HCID 62601Nickel acetate tetrahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-benzyloxy-4-methylnitrobenzene (1.1 g, 4.4 mmol) in tetrahydrofuran (25 mL) and methanol (50 mL) was added nickel acetate tetrahydrate (2.2 g, 8.7 mmol). The solution was cooled to 0° C. and sodium borohydride (0.66 g, 17.4 mmol) was added in small portions. After gas evolution had ceased, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate and concentrated ammonium hydroxide. The layers were separated and the organic phase was washed with ammonium hydroxide followed by saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated In vacuo to give 0.9 g (97%) of the title product as an off-white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and concentrated ammonium hydroxide
  3. customThe layers were separated
  4. washthe organic phase was washed with ammonium hydroxide
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated In vacuo

Sources & evidence

ORD record
ord-45acb0023692450f80e5692efd70658b
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Linked notes

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