5-(2-Methyl-2-nitropropoxy)salicylamide → 5-(2-Amino-2-methylpropoxy)salicylamide

HRID 4542Notes

Reaction equation

HRID 4542 reaction equation
[CH3:1][C:2]([N+:16]([O-])=O)([CH3:15])[CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1>CO>[NH2:16][C:2]([CH3:15])([CH3:1])[CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 137544245-(2-Methyl-2-nitropropoxy)salicylamide

Product 1

HCID 137544255-(2-Amino-2-methylpropoxy)salicylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.5 g 5-(2-methyl-2-nitropropoxy)salicylamide are hydrogenated in 150 ml of methanol at 40°-50° and 80 bar over 5 g of Raney nickel until hydrogen absorption ceases. By filtration and concentration of the filtrate by evaporation, crude 5-(2-amino-2-methylpropoxy)salicylamide is obtained, which, after standing for a relatively long period, crystallises from isopropanol and melts at 115°-117°.

Workup

  1. custom80 bar over 5 g of Raney nickel until hydrogen absorption
  2. filtrationBy filtration and concentration of the filtrate
  3. customby evaporation

Sources & evidence

ORD record
ord-f856ad7b2cbf4d718c46453c87b095f0
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Reaction notes

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