Diethyl Ether → 1-(2-Methylphenyl)-2,3-dihydropyrrolo[3,2-c]cinnoline

HRID 704568Notes

Reaction equation

HRID 704568 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[CH2:12][CH2:13]Cl.[NH2:15][C:16]1[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(OCC)C>O1CCOCC1>[CH3:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:15]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[N:4][C:3]=2[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7242O-ToluidineHCID 200727524-Chloro-3-(2-chloroethyl)cinnoline

Product 1

HCID 98166731-(2-Methylphenyl)-2,3-dihydropyrrolo[3,2-c]cinnoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-3-(2-chloroethyl)cinnoline (1.52 g, 0.0067 mol) and o-toluidine (1.43 g, 0.0134 mol) in 1,4 dioxan (20 ml) were heated under reflux for 20 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between chloroform and dilute sodium bicarbonate solution. The aqueous layer was extracted with chloroform (6×50 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a brown oil. The oil was purified by chromatography using chloroform (1 litre), chloroform/methanol (20:I) as eluant. The fractions containing the product were combined and evaporated under reduced pressure to give an oil. On trituration with diethyl ether a solid was obtained. The solid was collected by filtration and dried, 0.76 g. Recrystallization from ethyl acetate gave the title compound, 0.48 g, m.p. 140-142°.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between chloroform and dilute sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted with chloroform (6×50 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give a brown oil
  9. customThe oil was purified by chromatography
  10. additionThe fractions containing the product
  11. customevaporated under reduced pressure
  12. customto give an oil
  13. filtrationThe solid was collected by filtration
  14. customdried
  15. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-84573a0fc4154b3bbb249906fe9bf802
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Reaction notes

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