Hydrochloric Acid → HCID 20461938, compound

HRID 326050Notes

Reaction equation

HRID 326050 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.Cl>C(O)C>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 6075022,6-Dichloroquinoline

Product 1

HCID 20461938HCID 20461938, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,6-dichloroquinoline (6.0 g), 4-aminophenol (3.3 g), hydrochloric acid (3 g) and ethanol (100 ml) was stirred and refluxed for 10 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The ethyl acetate extracts on evaporation gave 4-[N-(6-chloro-2-quinolinyl)-amino]phenol (2.7 g) as a brown solid.

Workup

  1. temperaturerefluxed for 10 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe ethyl acetate extracts on evaporation

Sources & evidence

ORD record
ord-0e2be75bdab74687ab1bd0b5ab736122
Source dataset
uspto-grants-1984_04
Patent number
US04444584

Reaction notes

Loading…