Methanol → HCID 22397058, compound

HRID 1070474Notes

Reaction equation

HRID 1070474 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:8][C:7]2=O)([O-:3])=[O:2].ClS([N:23]=C=O)(=O)=O.CO>C(#N)C>[NH2:23][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 70918Chlorosulfonyl isocyanateHCID 2741052HCID 2741052, compound

Product 1

HCID 22397058HCID 22397058, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of methyl 1,4-dihydro-6-nitro-4-oxo-2-quinolinecarboxylate (3.72 g, 15 mmol) obtained in Example 131, Step 2 in acetonitrile (50 ml) was added chlorosulfonyl isocyanate (1.30 ml, 15 mol) and the mixture was refluxed under heating for 1 hr. The reaction mixture was cooled to room temperature and methanol was added, which was followed by concentration under reduced pressure. To the residue was added 2 mol/l aqueous sodium carbonate solution to allow suspending and the insoluble matter was collected by filtration. The insoluble matter was dried under reduced pressure at 80° C. to give methyl 4-amino-6-nitro-2-quinolinecarboxylate as crude brown crystals (3.23 g). This compound was used in the next reaction without purification.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. concentrationwhich was followed by concentration under reduced pressure
  4. additionTo the residue was added 2 mol/l aqueous sodium carbonate solution
  5. filtrationthe insoluble matter was collected by filtration
  6. customThe insoluble matter was dried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-fb4734718cc9414dbbf13943d8515050
Source dataset
uspto-grants-2005_06
Patent number
US06903094B2

Reaction notes

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