HCID 54000152, compound → HCID 15171525, compound

HRID 728200Notes

Reaction equation

HRID 728200 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]=[CH:26][CH:25]=[CH:24][N:23]3[CH:28]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH2:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:18][CH2:19][C:20]2[N:21]=[C:22]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]3[CH:28]=2)=[CH:10][C:9]=1[OH:8]

Participants

5

Reactant 2

HCID 54000152HCID 54000152, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15171525HCID 15171525, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[2-(3-benzyloxy-4-nitrophenyl)vinyl]imidazo[1,2-a]pyridine (40 g) in ethanol (600 ml) was hydrogenated over 10% palladium on carbon (10 g) at 4 to 6 atmospheric pressure of hydrogen gas for 4 hours at 40° to 70° C. The catalyst was removed by filtration an the filtrate was evaporated in vacuo to give a crystalline residue, which was washed with diethyl ether and dried to give 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (19.0 g).

Workup

  1. customThe catalyst was removed by filtration an the filtrate
  2. customwas evaporated in vacuo
  3. customto give a crystalline residue, which
  4. washwas washed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-161b2af48e6f4e4997d37111f4f39ff5
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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