HCID 54439733, compound → HCID 15171489, compound

HRID 728111Notes

Reaction equation

HRID 728111 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH:10][C:11](=[O:31])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23]CC3C=CC=CC=3)[CH:15]=2)[CH3:9])[CH:3]=1.[H][H]>[Pd].CO.O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH:10][C:11](=[O:31])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([OH:23])[CH:15]=2)[CH3:9])[CH:3]=1

Participants

6

Reactant 2

HCID 54439733HCID 54439733, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15171489HCID 15171489, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-2-[1-[3-benzyloxy-4-nitrocinnamoylamino)ethyl]pyridine (12.5 g) and 10% palladium on carbon (2 g) in a mixture of methanol (250 ml) and tetrahydrofuran (100 ml) was hydrogenated under one atmospheric pressure of hydrogen gas at ambient temperature for 4 hours. Insoluble material was filtered off, and the filtrate was evaporated in vacuo to give 4-methyl-2-[1-{3-(4-amino-3-hydroxyphenyl)propionamido}ethyl]pyridine (8.95 g).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1de506f3d37f49338fbf4f0f5aaf538f
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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