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

HRID 339553Notes

Reaction equation

HRID 339553 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]3[CH:18]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.CCOC(C)=O.C(Cl)Cl>CCO>[N:11]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:18][N:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=12

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 201134Imidazo(1,2-a)pyridine, 2-(p-nitrophenyl)-HCID 21226138Dichloromethane ethylacetate

Product 1

HCID 6969364-(Imidazo[1,2-a]pyridin-2-yl)anilineYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-(4-nitrophenyl)imidazo[1,2-a]pyridine (0.216 g, 0.90 mmol) and tin (II) chloride dihydrate (1.02 g, 4.52 mmol) in EtOH (25 ml) to give the title compound (0.144 g, 76%) as a pale yellow solid after work-up and flash chromatography (9:1 EtOAc/DCM).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fc3a2c82e0214ef6b0e19a48d062380a
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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