HCID 19823335, compound → HCID 15684639, compound

HRID 728198Notes

Reaction equation

HRID 728198 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:18][CH2:19][C:20]2[N:21]=[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]3[C:28]=2[CH3:29])[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)C1C=CC=CC=1>[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]=[CH:26][CH:25]=[CH:24][N:23]3[C:28]=2[CH3:29])=[CH:10][C:9]=1[OH:8]

Participants

5

Reactant 1

HCID 19823335HCID 19823335, compound

Product 1

HCID 15684639HCID 15684639, compoundYield 30.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon (3.0 g) was added to a mixture of 2-[2-(3-benzyloxy-4-nitrophenyl)ethyl]-3-methylimidazo[1,2-a]pyridine (6.5 g) in a mixture of methanol and tetrahydrofuran, and the mixture was subjected to catalytic reduction under. atmospheric pressure for 3 hours at ambient temperature. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by a column chromatography on silica gel, and eluted with a mixture of chloroform and methanol (9:1, V/V). The eluted fast fractions containing the desired product were collected and evaporated in vacuo to give 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-3-methylimidazo[1,2-a]pyridine (1.37 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by a column chromatography on silica gel
  4. washeluted with a mixture of chloroform and methanol (9:1, V/V)
  5. washThe eluted fast fractions
  6. additioncontaining the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a29b6de73ad4036a25a64b6d42a3c8a
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

Loading…