HCID 66761773, compound → HCID 66761517, compound

HRID 561804Notes

Reaction equation

HRID 561804 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH2:20][CH3:21])=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH2:20][CH3:21])=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

4

Reactant 1

HCID 66761773HCID 66761773, compound

Product 1

HCID 66761517HCID 66761517, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of propyl 2-[(1E)-3-methoxyprop-1-en-1-yl]quinoline-4-carboxylate from the previous step (1 eq.) in toluene (0.06 M) was added at 80° C. benzenesulfonyl hydrazide (3×1 eq.) over 3 h. The reaction mixture was diluted with EtOAc and washed sequentially with water, sat. aq. NaHCO3 and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a yellow oil. Purification by way of column chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

  1. washwashed sequentially with water, sat. aq. NaHCO3 and brine
  2. dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo
  3. customafforded the crude product as a yellow oil
  4. customPurification by way of column chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-187f244766cb413b8f54ef041fd6bd44
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…