Dimethylformamide → HCID 53927534, compound

HRID 1195747Notes

Reaction equation

HRID 1195747 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12](C(O)=O)[CH:13]=1)[NH:10][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][CH:7]2[C:23](O)=[O:24])([O-:3])=[O:2].[C:26](=[O:29])([O-:28])[O-].[K+].[K+].[CH3:32]I.CN([CH:37]=[O:38])C>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:26]([O:28][CH3:32])=[O:29])[CH:13]=1)[NH:10][CH:9]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:8][CH:7]2[C:23]([O:38][CH3:37])=[O:24])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15157749HCID 15157749, compound

Product 1

HCID 53927534HCID 53927534, compoundYield 82.3%

Procedure

A mixture of 6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline-4,8-dicarboxylic acid (8.92 g), potassium carbonate (10 g) and methyl iodide (5 ml) in DMF (30 ml) was stirred at room temperature for 2 hours, filtered and concentrated. The residue was dissolved in ethyl acetate (300 ml). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to give 7.92 g (82.3%) of the title compound as yellow crystals.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (300 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af35a0a272d2466ebfb0212adda26054
Source dataset
uspto-grants-1992_05
Patent number
US05112836

Reaction notes

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