Dimethylformamide → HCID 18321961, compound

HRID 564924Notes

Reaction equation

HRID 564924 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12]CC3C(Cl)=CC=C([N+]([O-])=O)C=3Cl)[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:25])[CH:3]=1.[CH3:26][N:27](C)[CH:28]=O>>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:25])[CH:3]=[C:2]2[N:27]([CH3:28])[CH3:26]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 22113037HCID 22113037, compound

Product 1

HCID 18321961HCID 18321961, compound

Procedure

A mixture of 4-chloro-8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylquinoline (200 mg) and N,N-dimethylformamide (3 ml) was heated under reflux for 18 hours. The reaction mixture was partitioned into ethyl acetate and saturated aqueous solution of sodium bicarbonate. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane-methanol) to give 8-hydroxy-2-methyl-4-dimethylaminoquinoline (26 mg) as a brownish powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe reaction mixture was partitioned into ethyl acetate and saturated aqueous solution of sodium bicarbonate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-f26fe980614b4df78c46bf09ab88182c
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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