Ammonia → HCID 17979845, compound

HRID 133094Notes

Reaction equation

HRID 133094 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=2)[N:3]=1.[NH3:17]>>[NH2:17][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:15][CH3:16])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 17979843HCID 17979843, compound2×

Product 1

HCID 17979845HCID 17979845, compound

Conditions

Temperature
125 °C

Procedure

0.75 g of 2-chloro-6-methoxy-3-nitroquinoline (compound C3) are dissolved in 70 ml of ethanolic ammonia solution and stirred at 125° C. for 6 h in an autoclave. After cooling to room temperature, the reaction mixture is concentrated in vacuo and the residue redissolved in 30 ml of ethyl acetate and extracted two times each with 30 ml of halfsaturated aqueous potassium carbonate solution. The organic phase is dried using magnesium sulfate, filtered and evaporated in vacuo. The residue is filtered over silica gel (dichloromethane/methanol 8:2). 0.64 g of the title compound are obtained as violet sold.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. dissolutionthe residue redissolved in 30 ml of ethyl acetate
  4. extractionextracted two times each with 30 ml of halfsaturated aqueous potassium carbonate solution
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. filtrationThe residue is filtered over silica gel (dichloromethane/methanol 8:2)

Sources & evidence

ORD record
ord-de829afd3db54dae8692fa048e4e70ba
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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