4-(3,7-Dimethylimidazo[1,2-a]pyridin-2-yl)-2-nitrophenol → 2-Amino-4-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)phenol

HRID 1731325Notes

Reaction equation

HRID 1731325 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([N+:19]([O-])=O)[CH:13]=1.[H][H]>C(O)C.O1CCCC1.[C].[Pd]>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([NH2:19])[CH:13]=1

Participants

6

Reactant 2

HCID 139224454-(3,7-Dimethylimidazo[1,2-a]pyridin-2-yl)-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 139224672-Amino-4-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)phenolYield 53.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,7-dimethyl-2-(4-hydroxy-3-nitrophenyl)imidazo[1,2-a]pyridine (2.6 g) in a mixture of ethanol (200 ml) and tetrahydrofuran (100 ml) was hydrogenated over 10% palladium-carbon (wet. 2.0 g) under an atomospheric pressure of hydrogen at ambient temperature for 3 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 3,7-dimethyl-2-(3-amino-4-hydro-xyphenyl)imidazo[1,2-a]pyridine (1.25 g). mp. 251°-253° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-8fcf612c37a24b6893ba3b06e9903f97
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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