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

HRID 272724Notes

Reaction equation

HRID 272724 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH3:13]>CO>[NH2:13][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[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 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-chloro-3-nitrophenyl)methanol (7.0 g, 37.32 mmoles), liquid NH3 (100 mL) and methanol (125 mL) were mixed in a sealed reactor. The temperature was set to 160° C., and the pressure became about 600 psi. After 16 hours, the reaction was cooled down. The high pressure was released. All the solvents were removed. The solid residual was purified by silica gel column to give 4.51 g of the above intermediate (72%). MS (DCI) m/e 169 (M+H)+; 1H NMR (300 MHz, CD3OD) □ 8.02 (d, J=1.70 Hz, 1H), 7.36 (dd, J=8.48, 2.03 Hz, 1H), 6.95 (d, J=8.48 Hz, 1H), 4.48 (s, 2H).

Workup

  1. customwas set to 160° C.
  2. temperaturethe reaction was cooled down
  3. customAll the solvents were removed
  4. customThe solid residual was purified by silica gel column

Sources & evidence

ORD record
ord-2e88ea8d83ff415bb870b001467a3348
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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