Methanol → HCID 10083527, compound

HRID 728120Notes

Reaction equation

HRID 728120 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)=[CH:6][CH:5]=1)([O-])=O.CO.[H][H]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 54521931HCID 54521931, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10083527HCID 10083527, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[2-(4-nitrophenyl)vinyl]-7-methylimidazo[1,2-a]pyridine (3.1 g) in a solution of methanol (100 ml) and tetrahydrofuran (100 ml) was hydrogenated over 10% palladium on carbon (1.0 g) under atmospheric pressure of hydrogen gas at ambient temperature for 3 hours. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with n-hexane to give a precipitate, which was collected by filtration and dried to give 2-[2-(4-aminophenyl)ethyl]-7-methylimidazo[1,2-a]pyridine (2.59 g).

Workup

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

Sources & evidence

ORD record
ord-e0df0a6bc7454d4c93e2e396f44ca435
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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