HCID 54508756, compound → HCID 15684642, compound

HRID 728109Notes

Reaction equation

HRID 728109 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]([CH3:28])[CH:25]=[CH:24][N:23]3[C:29]=2[CH3:30])[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)C1C=CC=CC=1.[H][H]>[Pd].CO.O1CCCC1>[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]([CH3:28])[CH:25]=[CH:24][N:23]3[C:29]=2[CH3:30])=[CH:10][C:9]=1[OH:8]

Participants

6

Reactant 2

HCID 54508756HCID 54508756, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15684642HCID 15684642, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon (10 g) was added to a mixture of 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-3,7-dimethylimidazo[1,2-a]pyridine (27.3 g) in methanol (200 ml) and tetrahydrofuran (200 ml) and the mixture was stirred at ambient temperature under atmospheric pressure of hydrogen gas. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with ethyl acetate and the precipitate was collected by filtration to give 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-3,7-dimethylimidazo[1,2-a]pyridine (13.8 ).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with ethyl acetate
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fed64991f8c646679a244cdbb4933128
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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