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

HRID 1462377Notes

Reaction equation

HRID 1462377 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 of 5-(2-methyl-2-nitro-propoxy)-salicylamide in 150 ml of methanol is hydrogenated at 40°-50° and 80 bars, with 5 g Raney Nickel, until the absorption of hydrogen ceases. Filtration and concentration by evaporation of the reaction mixture yield crude 5-(2-amino-2-methyl-propoxy)-salicylamide, which on prolonged standing crystallises from isopropanol, and melts at 115°-117°.

Workup

  1. customis hydrogenated at 40°-50°
  2. custom80 bars, with 5 g Raney Nickel, until the absorption of hydrogen ceases
  3. filtrationFiltration and concentration
  4. customby evaporation of the reaction mixture

Sources & evidence

ORD record
ord-f66121f4e8214b68bc91da5407a5b2c4
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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