Hydrochloric Acid → 7-Amino-8-methylquinoline-3-carbaldehyde

HRID 351345Notes

Reaction equation

HRID 351345 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:9].Cl.[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH:17](OC(C)C)([CH3:19])[CH3:18]>C(O)(C)C.C(OCC)(=O)C.O>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]2[C:4]([CH:18]=[C:17]([CH:11]=[O:14])[CH:19]=[N:9]2)=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 132052,6-Toluenediamine

Product 1

HCID 230223367-Amino-8-methylquinoline-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-methyl-1,3-benzenediamine (30.0 g, 246 mmol) and 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bis-tetrafluoroborate (263 g, 737 mmol) in isopropanol (500 ml) was heated under reflux with stirring for 16 hrs. and allowed to cool to room temperature. To the reaction solution was added 1N hydrochloric acid (500 ml). The mixture was stirred at 70° C. for 5 hrs. with heating and allowed to cool to room temperature. The resulting precipitate was collected and washed with water, acetonitrile and isopropyl ether. A suspension of the obtained precipitate (61.6 g) and potassium carbonate (170 g, 1.23 mol) in ethyl acetate (500 ml)-water (500 ml) was vigorously stirred with heating at 90° C. and allowed to cool to room temperature. The organic layer was separated, washed with saturated brine, dried over sodium sulfate and passed through silica gel (100 g) packed in a glass filter. The solvent was evaporated under reduced pressure and the obtained crude product was treated with isopropyl ether to give the title compound (35.4 g) as a powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. stirringThe mixture was stirred at 70° C. for 5 hrs
  4. temperaturewith heating
  5. temperatureto cool to room temperature
  6. customThe resulting precipitate was collected
  7. washwashed with water, acetonitrile and isopropyl ether
  8. stirringwas vigorously stirred
  9. temperaturewith heating at 90° C.
  10. temperatureto cool to room temperature
  11. customThe organic layer was separated
  12. washwashed with saturated brine
  13. dry with materialdried over sodium sulfate
  14. filtrationfilter
  15. customThe solvent was evaporated under reduced pressure
  16. customthe obtained crude product

Sources & evidence

ORD record
ord-99095e4ff0ba4959b49c73bcc1599ad2
Source dataset
uspto-grants-2007_02
Patent number
US07183415B2

Reaction notes

Loading…