Hydrochloric Acid → HCID 21220537, compound

HRID 1584733Notes

Reaction equation

HRID 1584733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17](=O)[CH2:16][CH:15]3[C:10]([C:11]4[CH:22]=[CH:21][N:20]=[CH:19][C:12]=4[CH2:13][CH2:14]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.O1CCCC1.B.Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:17][CH2:16][CH:15]3[C:10]([C:11]4[CH:22]=[CH:21][N:20]=[CH:19][C:12]=4[CH2:13][CH2:14]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 21220553HCID 21220553, compound

Product 1

HCID 21220537HCID 21220537, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Chlorophenyl)-4,4a,5,6-tetrahydropyrido[3,4-h]cinnolin-3(2H)-one (from Example 5 above; 66 mg) was placed in a flask under nitrogen. Borane tetrahydrofuran complex (1.0M in THF; 3 ml) was added and the solution stirred for 16 hours at ambient temperature. The mixture was added to methanol (3 ml) with stirring and then concentrated hydrochloric acid (0.5 ml) was added cautiously. The mixture was heated under reflux for 30 minutes, then cooled to room temperature and the volatiles removed on a rotary evaporator. The resultant product was partitioned between NaHCO3 (aqueous) and ethyl acetate. The aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were washed with brine, dried, filtered and concentrated to give a solid which was chromatographed eluting with ethyl acetate to give a solid which was recrystallised from isopropanol to yield the title compound as yellow crystals (14 mg).

Workup

  1. stirringwith stirring
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled to room temperature
  5. customthe volatiles removed on a rotary evaporator
  6. customThe resultant product was partitioned between NaHCO3 (aqueous) and ethyl acetate
  7. extractionThe aqueous phase was extracted twice more with ethyl acetate
  8. washThe combined organic layers were washed with brine
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give a solid which
  13. customwas chromatographed
  14. washeluting with ethyl acetate
  15. customto give a solid which
  16. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-d976b5298dc141a0a228ee1505f2bc3f
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

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