Phenol → N-Benzylpyrrolo[3,2-c]cinnoline

HRID 704575Notes

Reaction equation

HRID 704575 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][CH:8]=2.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:15]([N:22]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[N:5][C:4]=2[CH:3]=[CH:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 7504BenzylamineHCID 200727524-Chloro-3-(2-chloroethyl)cinnoline

Product 1

HCID 20072750N-Benzylpyrrolo[3,2-c]cinnoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(2-Chloroethyl)-4-chlorocinnoline (2 g, 0.0088 mol), benzylamine (4 g, 0.037 mol) and phenol (2 g, 0.0212 mol) were heated in an oil bath at 160° for 20 hours. The reaction had not gone to completion so the temperature was raised to 190° for a further 6 hours. The reaction mixture was dissolved in chloroform (300 ml) and extracted with 2N sodium hydroxide (3×100 ml). The chloroform extracts were washed with water (100 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was purified by chromatography using chloroform as eluant. The fractions containing the product were combined and evaporated to dryness to give a brown solid. Recrystallization from isopropyl alcohol gave the title compound, 0.5 g, m.p. 190-192°.

Workup

  1. temperaturewas raised to 190° for a further 6 hours
  2. extractionextracted with 2N sodium hydroxide (3×100 ml)
  3. washThe chloroform extracts were washed with water (100 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe oil was purified by chromatography
  9. additionThe fractions containing the product
  10. customevaporated to dryness
  11. customto give a brown solid
  12. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-f28e97e928a049afbcb1f7ec23971dfa
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Reaction notes

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