4-Amino-m-cresol → 1-(4-Hydroxy-2-methylphenyl)-2,3-dihydropyrrolo[3,2-c]-cinnoline hydrochloride

HRID 704574Notes

Reaction equation

HRID 704574 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[CH2:12][CH2:13]Cl.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:23])[CH:17]=1>O1CCOCC1>[ClH:1].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:2]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[N:5]=[N:4][C:3]=3[CH2:12][CH2:13]2)=[C:18]([CH3:23])[CH:17]=1

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 200727524-Chloro-3-(2-chloroethyl)cinnoline

Product 1

HCID 200727551-(4-Hydroxy-2-methylphenyl)-2,3-dihydropyrrolo[3,2-c]-cinnoline hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-3-(2-chloroethyl)cinnoline (1 g, 0.0044 mol) and 4-hydroxy-2-methylphenylamine (0.54 g, 0.0044 mol) in 1,4 dioxan (20 ml) were heated under reflux for 20 hours. The solid obtained was collected by filtration and dried. Recrystallization from ethanol gave the title compound, 0.4 g, m.p. >300°

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solid obtained
  3. filtrationwas collected by filtration
  4. customdried
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-a1afc8196a0f48aaa3b96050e5d8c96b
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Reaction notes

Loading…