Stannous chloride dihydrate → 4-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline

HRID 339555

Reaction equation

HRID 339555 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.O.O.[Sn](Cl)Cl>CCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 7499176-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)anilineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 6-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine (0.423 g, 1.67 mmol) and tin (II) chloride dihydrate (1.89 g, 8.36 mmol) in EtOH (45 ml) to give the title compound (0.216 g, 58%) as a pale orange solid, after work-up and flash chromatography (EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5cde5669826a48ddae31c560af713240
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Linked notes

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