Ammonia → (4-Amino-3-nitrophenyl)methanol

HRID 1758993Notes

Reaction equation

HRID 1758993 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH3:13]>CO>[NH2:13][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 919334-Chloro-3-nitrobenzyl alcohol

Product 1

HCID 12902831(4-Amino-3-nitrophenyl)methanolYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

Fifty grams (0.27 mole) of 4-chloro-3-nitrobenzyl alcohol, 250 ml. of methanol and 200 ml. of liquid ammonia were loaded into a cold autoclave. The autoclave was sealed and heated to a temperature of 150° C. The reaction was continued for 6 hours. After cooling the autoclave was vented and the reaction mixture was evaporated in vacuo. The residue was taken up in ether and the ether solution was filtered to separate the ammonium chloride. The ether filtrate was evaporated in vacuo to yield a solid product. The product was recrystallized from 2-B ethanol/ethyl acetate to give 23.6 g. (52 percent yield) of 4-amino-3-nitrobenzyl alcohol, mp. 100°-101° C.

Workup

  1. customThe autoclave was sealed
  2. temperatureAfter cooling the autoclave
  3. customthe reaction mixture was evaporated in vacuo
  4. filtrationthe ether solution was filtered
  5. customto separate the ammonium chloride
  6. customThe ether filtrate was evaporated in vacuo
  7. customto yield a solid product
  8. customThe product was recrystallized from 2-B ethanol/ethyl acetate
  9. customto give 23.6 g

Sources & evidence

ORD record
ord-241715751bf949769b545c0899758020
Source dataset
uspto-grants-1982_07
Patent number
US04338329

Reaction notes

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