2,3-Dimethyl-8-(2,6-dimethylbenzylamino)-7-nitroimidazo[1,2-a]pyridine → 7-Amino-2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine

HRID 1006685Notes

Reaction equation

HRID 1006685 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[C:8]([N+:20]([O-])=O)[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24]>[Ni].C(O)C>[NH2:20][C:8]1[CH:7]=[CH:6][N:5]2[C:23]([CH3:24])=[C:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[NH:10][CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19]

Participants

4

Reactant 1

HCID 226726012,3-Dimethyl-8-(2,6-dimethylbenzylamino)-7-nitroimidazo[1,2-a]pyridine

Product 1

HCID 226725947-Amino-2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridineYield 97.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-7-nitroimidazo[1,2-a]pyridine (45 mg, 0.139 mmol) Raney-Ni (0.1 g) and ethyl alcohol 4 ml was hydrogenated (H2, 1 bar) at 40° C. for 3 h. The mixture was filtrated using a small amount of silica gel and the solvent was removed under reduced pressure. 40 mg (97%) of the title compound was obtained.

Workup

  1. customat 40° C.
  2. customfor 3 h
  3. filtrationThe mixture was filtrated
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c95156ba7c6e4a2f88fcdbc2d57cfb57
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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