Sodium borohydride → Benzeneethanol,2-amino-5-nitro-

HRID 1251294Notes

Reaction equation

HRID 1251294 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH:11]([OH:13])[CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 112523331-(2-amino-5-nitrophenyl)ethanone

Product 1

HCID 11148092Benzeneethanol,2-amino-5-nitro-Yield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 5 (27.02 g, 150 mmole) in methanol (150 mL) at 4° C. was added sodium borohydride (5.67 g, 150 mmole) over a period of 0.25 h. After the addition was complete, the solution was warmed to room temperature and stirred for 0.25 h. The methanol was evaporated under vacuum. Water (150 mL) was added to the residue and the precipitate was filtered, washed with cold water, and air dried to afford 1-(2-amino-5-nitro-phenyl)-ethanol 6 (27.0 g, 99% yield). 1HNMR (400 MHz, DMSO-d6) δ1.27 (d, 3H, J=6.3), 4.77-4.82 (m, 1H), 5.36 (d, 1H, J=4.3 Hz), 6.50 (s, 2H), 6.63 (d, 1H, J=9.0 Hz), 7.85 (dd, 1H, J=2.8, 9.0 Hz), 8.07 (d, 1H, J=2.6); MS m/z 182 (M+).

Workup

  1. additionAfter the addition
  2. customThe methanol was evaporated under vacuum
  3. additionWater (150 mL) was added to the residue
  4. filtrationthe precipitate was filtered
  5. washwashed with cold water, and air
  6. customdried

Sources & evidence

ORD record
ord-f04e5e98c59148a2a28022b3c1068c5a
Source dataset
uspto-grants-2002_01
Patent number
US06342079B1

Reaction notes

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