Hydrochloric Acid → 2-Amino-5-nitrobenzyl alcohol

HRID 2286857Notes

Reaction equation

HRID 2286857 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>C(O)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2792602-Amino-5-nitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 30187062-Amino-5-nitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-amino-5-nitrobenzaldehyde (6.0 g.) in ethanol (250 ml.) was stirred at ambient temperature while sodium borohydride (1.6 g.) was added in small portions, and the reaction mixture was stirred for 1 hour. The reaction mixture was made acid with 2 N hydrochloric acid to destroy the excess of sodium borohydride, and then basified to pH 8 to 9 with solid sodium carbonate and extracted with diethyl ether (3×200 ml.). The extracts were combined and dried, the solvent was evaporated and the residue was crystallised from water (about 200 ml.) to give the required 2-amino-5-nitrobenzyl alcohol, m.p. 141°-142° C.;

Workup

  1. additionwas added in small portions
  2. customto destroy the excess of sodium borohydride
  3. extractionextracted with diethyl ether (3×200 ml.)
  4. customdried
  5. customthe solvent was evaporated
  6. customthe residue was crystallised from water (about 200 ml.)

Sources & evidence

ORD record
ord-77f4acd93ce44481bdbfc96ce8c1fe68
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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