Hydrochloric Acid → HCID 13472703, compound

HRID 326052Notes

Reaction equation

HRID 326052 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.Cl>C(#N)C>[N+:12]([C:11]1[C:2]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 126639372-Chloro-3-nitroquinoline

Product 1

HCID 13472703HCID 13472703, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-3-nitroquinoline [0.35 g, prepared by the method of Kaneko, Chem. Pharm. Bull. (Tokyo) 7, 273 (1959)], 4-aminophenol (0.6 g), acetonitrile (20 ml) and dilute hydrochloric acid (30 ml, 1 M) was heated under reflux for 16 hours. The resulting deep orange solution was concentrated under reduced pressure (to 20 ml) and extracted with ethyl acetate (50 ml). The ethyl acetate extract was dried and evaporated to give 4-[N-(3-nitro-2-quinolinyl)amino]phenol as an organge solid, mp 190° C.

Workup

  1. customprepared by the method of Kaneko, Chem
  2. temperatureunder reflux for 16 hours
  3. concentrationThe resulting deep orange solution was concentrated under reduced pressure (to 20 ml)
  4. extractionextracted with ethyl acetate (50 ml)
  5. extractionThe ethyl acetate extract
  6. customwas dried
  7. customevaporated

Sources & evidence

ORD record
ord-529f777fa6f04fbabf41d169437e7d26
Source dataset
uspto-grants-1984_04
Patent number
US04444584

Reaction notes

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