HCID 54191570, compound → HCID 15684641, compound

HRID 728108Notes

Reaction equation

HRID 728108 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[CH:29]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[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]([CH3:28])[CH:25]=[CH:24][N:23]3[CH:29]=2)=[CH:10][C:9]=1[OH:8]

Participants

6

Reactant 2

HCID 54191570HCID 54191570, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15684641HCID 15684641, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]-7-methylimidazo[1,2-a]pyridine in a mixture of methanol (300 ml) and tetrahydrofuran (300 ml) was hydrogenated over 10% palladium on carbon (5.0 g) under atmospheric pressure of hydrogen gas at ambient temperature. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with diethyl ether to give a precipitate which was collected by filtration and dried to give 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-7-methylimidazo[1,2-a]pyridine (20.67 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with diethyl ether
  4. customto give a precipitate which
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-3dd69ffb30904558ac7c8a6483e45637
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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