Ammonia → HCID 17979855, compound

HRID 133093Notes

Reaction equation

HRID 133093 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]([CH3:15])[CH:8]=2)[N:3]=1.[NH3:16]>>[NH2:16][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 17979840HCID 17979840, compound2×

Product 1

HCID 17979855HCID 17979855, compound

Conditions

Temperature
130 °C

Procedure

2.0 g of 2-chloro-6-methyl-3-nitroquinoline (compound C2) is dissolved in 100 ml of ethanolic ammonia solution and stirred at 130° C. for 6 h in an autoclave. After cooling to from temperature, the reaction mixture is concentrated in vacuo and the residue redissolved in 50 ml of ethyl acetate and extracted two times each with 50 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). 1.5 g of the title compound are obtained as violet solid.

Workup

  1. temperatureAfter cooling to from temperature
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. dissolutionthe residue redissolved in 50 ml of ethyl acetate
  4. extractionextracted two times each with 50 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)

Sources & evidence

ORD record
ord-5ca3cd5ce2bd4ad48079e66e2d66ac86
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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