Dimethylamine → Dimethyl-(6-methyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-4-yl)-amine

HRID 729086Notes

Reaction equation

HRID 729086 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[C:12](Cl)[C:11]=2[CH2:10][CH2:9]1.[CH3:23][NH:24][CH3:25]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[C:12]([N:24]([CH3:25])[CH3:23])[C:11]=2[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 157498191-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

Product 1

HCID 15749825Dimethyl-(6-methyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-4-yl)-amineYield 63%

Procedure

1-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (1.5 g. 4.9 mmol) and dimethylamine (33% in ethanol. 150 ml) were heated to 180° C. in a pressure vessel for 18 hours, then evaporated, taken up in dichloromethane, washed with sodium bicarbonate, dried and evaporated. Crystallisation from aqueous ethanol gave 1-(2-methylphenyl)-4-dimethylamino- 6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (0.97 g, 63%), m.p. 120°-121°.

Workup

  1. customevaporated
  2. washwashed with sodium bicarbonate
  3. customdried
  4. customevaporated
  5. customCrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-3b41a7396bbe459ab5d0fffcb3748dde
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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