4-Amino-m-cresol → HCID 44366651, compound

HRID 729098Notes

Reaction equation

HRID 729098 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15]Cl.[OH:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([CH3:25])[CH:19]=1>C(O)CCC>[OH:17][C:18]1[CH:24]=[CH:23][C:21]([N:22]2[C:3]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N:6]=[C:5]([CH3:13])[C:4]=3[CH2:14][CH2:15]2)=[C:20]([CH3:25])[CH:19]=1

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 67906098HCID 67906098, compound

Product 1

HCID 44366651HCID 44366651, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-chloro-3-chloroethyl-2-methylquinoline hydrochloride (1.28 g, 4,6 mmol) and 4-hydroxy-2-methylaniline (1.13 g. 9.2 mmol) in n-butanol(20 ml) was heated at reflux under a nitrogen atmosphere for 20 hours, thenevaporated. Chromatography (silica gel, 5-7% methanolic ammonia in dichloromethane) and recrystallisation from aqueous methanol gave 1-(4-hydroxy2-methylphenyl)-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (0.16 g), m.p. 315°-318°.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 20 hours
  2. customChromatography (silica gel, 5-7% methanolic ammonia in dichloromethane) and recrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-a89c24d6a26848f8befb9c785cc522df
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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