2-Toluidine hydrochloride → 1-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline

HRID 704572

Reaction equation

HRID 704572 reaction equation
Cl[CH2:2][CH2:3][C:4]1[N:5]=[N:6][C:7]2[C:12]([C:13]=1Cl)=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:15].Cl.[NH2:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>O1CCOCC1>[CH3:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:17]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([CH3:15])[C:7]=3[N:6]=[N:5][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 124842-Toluidine hydrochlorideHCID 200727624-Chloro-3-(2-chloroethyl)-8-methylcinnoline

Product 1

HCID 200727571-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(2-Chloroethyl)-4-chloro-8-methylcinnoline (2.5 g, 0.01mol) and o-toluidine hydrochloride (1.4 g, 0.01 mol) in 1,4 dioxan (20 ml) were heated under reflux for 20 hours. The solvent was evaporated under reduced pressure to give an oil. The oil was partitioned between chloroform and dilute sodium carbonate solution and extracted further with chloroform (4×100 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated to give an oil. The oil was purified by column chromatography using dichloromethane then chloroform as eluant. The solid obtained was recrystallized from diethyl ether/ dichloromethane to give the title compound, 0.6 g, m.p. 135-137°.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customto give an oil
  4. customThe oil was partitioned between chloroform and dilute sodium carbonate solution
  5. extractionextracted further with chloroform (4×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give an oil
  10. customThe oil was purified by column chromatography
  11. customThe solid obtained
  12. customwas recrystallized from diethyl ether/ dichloromethane

Sources & evidence

ORD record
ord-7a2061e706aa463688322487297d07ec
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Linked notes

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