Hydrazine hydrate (1:1) → HCID 20393408, compound

HRID 1863103Notes

Reaction equation

HRID 1863103 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]=[C:8]([CH:16]=[CH2:17])[CH:7]=[CH:6]2.O.NN>[Ni].C1(C)C=CC=CC=1>[NH2:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[C:8]([CH2:16][CH3:17])[CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 615443HCID 615443, compound

Product 1

HCID 20393408HCID 20393408, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 9.6 g (0.04 mole) of 6-methoxy-8-nitro-2-vinylquinoline, 5 g (wet weight, washed with ethanol) of Raney nickel catalyst and 250 ml of toluene-95% ethanol (1:1) was added 25 ml of 85% hydrazine hydrate in portions, and after the vigorous reaction was over the mixture was heated under reflux for 5 hr. The condensor was removed and the mixture heated (ethanol added) until the vapors were faintly alkaline. The mixture was cooled, filtered over diatomaceous earth, and the filtrate concentrated in vacuo. The oily residue was dissolved in anhydrous ether and treated with HBr gas. The hydrobromide precipitated as a yellow powder and was recrystallized from ethanol-chloroform. The yield was 6.6 g (56%) of the desired 8-amino-2-ethyl-6-methoxyquinoline hydrobromide, mp 239°-241°. Rf : 0.62 (19.2 ethyl acetate-diethylamine), 0.67 (19:1 ethanol-diethylamine), 0.74 (19:1 methanol-diethylamine).

Workup

  1. customafter the vigorous reaction
  2. temperaturewas heated
  3. temperatureunder reflux for 5 hr
  4. customThe condensor was removed
  5. temperaturethe mixture heated
  6. addition(ethanol added) until the vapors
  7. temperatureThe mixture was cooled
  8. filtrationfiltered over diatomaceous earth
  9. concentrationthe filtrate concentrated in vacuo
  10. dissolutionThe oily residue was dissolved in anhydrous ether
  11. additiontreated with HBr gas
  12. customThe hydrobromide precipitated as a yellow powder
  13. customwas recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-cdda5f095dad43e4bff084c116eda840
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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