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

HRID 46699Notes

Reaction equation

HRID 46699 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-9e48597510a1436e961be6ced01f643f
Source dataset
uspto-grants-1979_11
Patent number
US04174454

Reaction notes

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