Dimethylformamide → HCID 15035244, compound

HRID 1656444Notes

Reaction equation

HRID 1656444 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:16]=1[OH:25].[CH3:26]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].CI>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:16]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135625381HCID 135625381, compound

Product 1

HCID 15035244HCID 15035244, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloro-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-nitroquinoline (1.20 g), N,N-dimethylformamide (20 ml), potassium carbonate powder (0.92 g) and methyl iodide (0.41 ml) was stirred for 10 mins. at 0° C. and for 2 hrs. at room temperature, and then diluted with water, extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was recrystallized from methanol to give 6-chloro-4-(2,3,4-trimethoxyphenyl)-3-nitroquinoline as yellow crystals (1.12 g, 89.6%). m.p. 114°-116° C.

Workup

  1. waitat 0° C. and for 2 hrs
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-8ef7167654ad4ed686c0216783851688
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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