O-Toluidine → HCID 44366622, compound

HRID 729079Notes

Reaction equation

HRID 729079 reaction equation
[CH3:1][C:2]1[C:11]([CH2:12][CH2:13]Cl)=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>C(O)C>[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[N:19]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([CH3:1])[C:11]=2[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 8203204-chloro-3-(2-chloroethyl)-2-methylquinoline

Product 1

HCID 44366622HCID 44366622, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-3-(2-chloroethyl)-4-chloroquinoline (45 g, 0.16 mol), 2-methylaniline (35 ml, 0.32 mol) and ethanol (300 ml) were heated to 150° C. in a pressure vessel for 17 hours, then concentrated in vacuo. The product crystallised as the hydrochloride salt. Conversion to free base and recrystallisation from ethyl acetate yielded 1-(2-methylphenyl)-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (19.1 g, 43%), m.p. 148°-150°.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product crystallised as the hydrochloride salt
  3. customConversion to free base and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-22c83cafbf924138ae7553a64ae12124
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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