2-Methyl-4-methoxyaniline → HCID 44366347, compound

HRID 729080Notes

Reaction equation

HRID 729080 reaction equation
Cl.[CH3:2][C:3]1[C:12]([CH2:13][CH2:14]Cl)=[C:11](Cl)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>C(O)C>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:11]3[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:4]=[C:3]([CH3:2])[C:12]=3[CH2:13][CH2:14]2)=[C:21]([CH3:26])[CH:20]=1

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 67906098HCID 67906098, compound

Product 1

HCID 44366347HCID 44366347, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-3-(2-chloroethyl)-4-chloroquinoline hydrochloride (5.53 g, 20 mmol) and 4-methoxy-2-methylaniline (5.15 ml, 40 mmol) in ethanol (100 ml)were heated at 170° C. in a pressure vessel for 24 hours, then the solvent evaporated, the crude product taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Chromatography (silica gel, 2% methanolic ammonia in dichloromethane) and recrystallisation from aqueous methanol gave 1-(4-methoxy-2-methylphenyl)-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (2.04 g, 22 %), m.p. 115°-117°.

Workup

  1. customthe solvent evaporated
  2. washwashed with aqueous sodium bicarbonate
  3. customdried
  4. customevaporated
  5. customChromatography (silica gel, 2% methanolic ammonia in dichloromethane) and recrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-ba40f0b1b2d54ef38c2abb5b8bc89b7e
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

Loading…