Methanol → 2-Hydrazino-4-phenylquinoline

HRID 1974051Notes

Reaction equation

HRID 1974051 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.[NH2:19][NH2:20].CO>C(O)C>[NH:19]([C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 23066872-Chloro-4-phenylquinoline

Product 1

HCID 204855962-Hydrazino-4-phenylquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In carrying out the process of the present invention, a 2-chloro-4-phenylquinoline I is heated with hydrazine hydrate. In the preferred embodiment of this invention, the reaction is carried out at the reflux temperature of the mixture; however, temperatures between 25° and 118° C. with a reaction time of 1 to 18 hours are operative. A solvent, such as lower alkanol, e.g., methanol, ethanol, 1- and 2-propanol can be used but is not necessary. In the preferred embodiment of the invention, one hour reflux under nitrogen is sufficient. At the termination of the reaction, the mixture is concentrated, poured into water and the insoluble product collected on a filter. Purification is carried out by conventional means such as extraction, chromatography or more commonly recrystallization to obtain the corresponding 2-hydrazino-4-phenylquinoline II.

Workup

  1. customtemperatures between 25° and 118° C.
  2. customwith a reaction time of 1 to 18 hours
  3. temperatureIn the preferred embodiment of the invention, one hour reflux under nitrogen
  4. customAt the termination of the reaction
  5. concentrationthe mixture is concentrated
  6. additionpoured into water
  7. customthe insoluble product collected on a filter
  8. customPurification
  9. extractionis carried out by conventional means such as extraction, chromatography or more commonly recrystallization

Sources & evidence

ORD record
ord-371a46b28bf3486ab0cbded98643bedd
Source dataset
uspto-grants-1976_12
Patent number
US04000151

Reaction notes

Loading…