Ammonium Chloride → N-(3-Hydroxymethylphenyl)hydroxylamine

HRID 845588Notes

Reaction equation

HRID 845588 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8])([O-])=[O:2].[NH4+].[Cl-]>C(O)C.[Zn]>[OH:8][CH2:7][C:6]1[CH:5]=[C:4]([NH:1][OH:2])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 692673-Nitrobenzyl alcohol

Product 1

HCID 20131568N-(3-Hydroxymethylphenyl)hydroxylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-nitrobenzyl alcohol (90) (1.53 g, 10 mmol) and NH4Cl (1.3 g, 24.3 mmol) in 86% aqueous ethanol (88 mL) was added zinc powder (2.6 g, 39.8 mmol). The resulting mixture was stirred vigorously at room temperature for 50 min. The mixture was filtered, and the solvent was poured into dichloromethane (450 mL). The solution was washed with water (10 mL) and dried (MgSO4), and the solvent was concentrated to about 15 mL with a rotary evaporator. The resulting solution was used in subsequent reactions without further purifications.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe solvent was poured into dichloromethane (450 mL)
  3. washThe solution was washed with water (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationthe solvent was concentrated to about 15 mL with a rotary evaporator

Sources & evidence

ORD record
ord-a5c80205576c4b799c20505a20079459
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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