HCID 68750609, compound → HCID 68749629, compound

HRID 624260Notes

Reaction equation

HRID 624260 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=2)[NH:9][C:8](=[O:17])[CH:7]=1)[CH2:2][CH:3]=[CH2:4]>C1C=CC=CC=1>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:17])[CH:7]3[CH2:4][CH:3]4[CH2:2][CH2:1][O:5][C:6]34[C:15]=2[CH:14]=1

Participants

3

Reactant 1

HCID 68750609HCID 68750609, compound

Product 1

HCID 68749629HCID 68749629, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-(but-3-enyloxy)-6-chloroquinolin-2(1H)-one (600 mg, 2.403 mmol) in benzene (240 mL) was placed under a 450 W Hg UV lamp (fitted with a condenser for cooling) and stirred for 4 days (96 hours). The mixture was then cooled, concentrated in vacuo, and taken up in ˜75 mL of methylene chloride (with mild heating to dissolve as much as possible). The sample, which was a mixture of regioisomers, was purified by column chromatography. Concentration of the compound that eleuted second provided the title compound.

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated in vacuo
  3. additiona mixture of regioisomers
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f026bbb73f284a08866fb6651af088f5
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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