Methane → 6-Amino-8-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 704619Notes

Reaction equation

HRID 704619 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.C.O.NN>C(O)C>[NH2:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([CH3:1])[CH:3]=1)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 297Methane2×HCID 24654Hydrazine hydrate (1:1)2×HCID 200728738-methyl-6-nitro-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 146275496-Amino-8-methyl-3,4-dihydroquinolin-2(1H)-oneYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 8-methyl-6-nitro-3,4-dihydro-2(1H)-quinolinone (25 g), activated charcoal (8 g) and ferric chloride (2.5 g) in ethanol (700 ml) was dropwise added hydrazine monohydrate (30 g) over the period of 20 minutes at 77° C., and the mixture was stirred for 1 hour. Then, to the reaction mixture were added activated charcoal (3 g) and ferric chloride (1.5 g) and was dropwise added hydrazine monohydrate (10 g). After refluxed for 1.5 hours, the reaction mixture was filtered and the insoluble material was washed with ethanol and a mixture of ethanol and chloroform successively. The solvent was evaporated under reduced pressure and the residue was dissolved in chloroform. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 6-amino-8-methyl-3,4-dihydro-2(1H)-quinolinone (19.5 g).

Workup

  1. customover the period of 20 minutes
  2. customat 77° C.
  3. temperatureAfter refluxed for 1.5 hours
  4. filtrationthe reaction mixture was filtered
  5. washthe insoluble material was washed with ethanol
  6. additiona mixture of ethanol and chloroform successively
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionthe residue was dissolved in chloroform
  9. washThe organic layer was washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-063eb6e68c32461894775ea1d9530938
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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