HCID 67836422, compound → HCID 15684647, compound

HRID 728145Notes

Reaction equation

HRID 728145 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][C:20]2[N:21]=[C:22]3[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[CH:24][N:23]3[C:31]=2[CH3:32])[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)C1C=CC=CC=1.[H][H]>CN(C)C=O.[Pd]>[NH2:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:18][CH2:19][C:20]2[N:21]=[C:22]3[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[CH:24][N:23]3[C:31]=2[CH3:32])=[CH:10][C:9]=1[OH:8]

Participants

5

Reactant 2

HCID 67836422HCID 67836422, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15684647HCID 15684647, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-7-ethoxy-3-methylimidazo[1,2-a]pyridine (3.8 g) in N,N-dimethylformamide (80 ml) was subjected to catalytic reduction over 10% palladium on carbon (1.9 g) under atmospheric pressure of hydrogen gas at 40° to 60° C. for hours. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with a mixture of diethyl ether and diisopropyl ether and the precipitate was collected by filtration to give 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-7-ethoxy-3-methylimidazo[1,2-a]pyridine (1.73 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with a mixture of diethyl ether and diisopropyl ether
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-1d2b97bf4d524af2a7a5fe2793fc2358
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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