Quinoline → Ethyl 3-aminopent-4-enoate

HRID 1387465Notes

Reaction equation

HRID 1387465 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[H][H].[CH2:13]([O:15][C:16](=[O:22])[CH2:17][CH:18]([NH2:21])[C:19]#[CH:20])[CH3:14]>CCO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH2:13]([O:15][C:16](=[O:22])[CH2:17][CH:18]([NH2:21])[CH:19]=[CH2:20])[CH3:14]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 22006121Ethyl 3-amino-4-pentynoateHCID 178418361HCID 178418361, compound

Product 1

HCID 10057602Ethyl 3-aminopent-4-enoate

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5% Pd/BaSO4 (0.025 g) and quinoline (0.30 mL) was stirred under a balloon of hydrogen for 30 minutes. 3-Amino-pent-4-ynoic acid ethyl ester (18-1 (for preparation, see J. A. Zablocki, et al., J. Med. Chem., 1995, 38, 2378-2394) (1.77 g, 10.0 mmol) in EtOH (15 mL) was added and the solution stirred for an additional 2.5 hours. The solution was filtered through a pad of celite and concentrated in vacuo to provide 2.65 g of crude product 18-2.

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d489dfdf3f94acca6f8179a46ce7dcc
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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