4-Methylquinoline → HCID 86759012, compound

HRID 1369368Notes

Reaction equation

HRID 1369368 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(OCC)(=O)C>[Br-:12].[CH2:19]([O:18][C:16]([CH2:15][CH2:14][CH2:13][C:3]1[CH:2]=[NH+:1][C:11]2[C:6]([C:4]=1[CH3:5])=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 102854-MethylquinolineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 86759012HCID 86759012, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 1.43 g of lepidine and 2.5 g of ethyl 4-bromobutyrate is heated at 140-150° C. for 1.5 hours. The mixture is cooled to room temperature and stirred in 100 mL of ethyl acetate for 3 hours and filtered to yield 2.6 g of Compound 5.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-48e255e1c8ad4316bf6796475436f341
Source dataset
uspto-grants-2003_06
Patent number
US06579718B1

Reaction notes

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