2-Methyl-4-methoxyaniline → 1-(4-Methoxy-2-methylphenyl)-4-methyl-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 729099Notes

Reaction equation

HRID 729099 reaction equation
Cl.[CH3:2][C:3]1[C:12]([CH2:13][CH2:14]Cl)=[C:11](Cl)[C:10]2[C:5](=[C:6]([O:17][CH3:18])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[C:23]([CH3:28])[CH:22]=1>CC(O)C>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([N:25]2[C:11]3[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([O:17][CH3:18])[C:5]=4[N:4]=[C:3]([CH3:2])[C:12]=3[CH2:13][CH2:14]2)=[C:23]([CH3:28])[CH:22]=1

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 679057642-Methyl-3-(2-chloroethyl)-4-chloro-8-methoxyquinoline hydrochloride

Product 1

HCID 443666371-(4-Methoxy-2-methylphenyl)-4-methyl-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinolineYield 18.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-methyl-3-(2-chloroethyl)-4-chloro-8-methoxyquinoline hydrochloride (15.33 g, 50 mmol), 4-methoxy-2-methylaniline (9.0 ml. 70 mmol) and 2-propanol (200 ml) was heated at reflux for 2 days, then evaporated. The crude product was triturated with ether then recrystallised twice from aqueous ethanol to give the title compound (3.16g), m.p. 163°-167°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customevaporated
  4. customThe crude product was triturated with ether
  5. customthen recrystallised twice from aqueous ethanol

Sources & evidence

ORD record
ord-a0006b186ff041ef9e89de2aa2072fda
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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