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

HRID 26380Notes

Reaction equation

HRID 26380 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. After cooling, the autoclave was vented and the volatile constituents removed by evaporation in vacuo. The residue was taken up in ether and the ether solution was filtered to remove ammonium chloride which had precipitated. The ether filtrate was evaporated in vacuo to yield a solid product. The product was recrystallized from 95% 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
  3. customthe volatile constituents removed by evaporation in vacuo
  4. filtrationthe ether solution was filtered
  5. customto remove ammonium chloride which
  6. customhad precipitated
  7. customThe ether filtrate was evaporated in vacuo
  8. customto yield a solid product
  9. customThe product was recrystallized from 95% ethanol/ethyl acetate
  10. customto give 23.6 g

Sources & evidence

ORD record
ord-5d6d1a3ce7c44d7987150bcf3e698aa6
Source dataset
uspto-grants-1979_04
Patent number
US04150028

Reaction notes

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