Dimethylformamide → HCID 18321961, compound

HRID 864574Notes

Reaction equation

HRID 864574 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-c1a811afd217403d94de3ebc1f6ea8c1
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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