3-(3-methyl-3-nitro-butyl)-3H-benzoxazol-2-one → 3-(3-amino-3-methyl-butyl)-3H-benzoxazol-2-one

HRID 33372Notes

Reaction equation

HRID 33372 reaction equation
[CH3:1][C:2]([N+:16]([O-])=O)([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14]>C(O)C.[Ni]>[NH2:16][C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14]

Participants

4

Reactant 1

HCID 574358403-(3-methyl-3-nitro-butyl)-3H-benzoxazol-2-one

Product 1

HCID 574358383-(3-amino-3-methyl-butyl)-3H-benzoxazol-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

11.0 g 3-(3-methyl-3-nitro-butyl)-3H-benzoxazol-2-one from the reaction described above are dissolved in 130 mL ethanol and hydrogenated with Raney nickel as catalyst at 5 bar for 20 hours. The catalyst is filtered off and the filtrate is freed from the solvent. 10% ethanolic hydrochloric acid is added, the solvent is distilled off and the residue is stirred in an acetone/diethyl ether mixture. White solid. Yield: 6.0 g (77% over 2 steps, hydrochloride); melting range=145-147° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. addition10% ethanolic hydrochloric acid is added
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-c0abc04fb7094e70a537e169bf77c463
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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