Methanol → HCID 21220522, compound

HRID 1584732Notes

Reaction equation

HRID 1584732 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.CO>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 21220552HCID 21220552, compound

Product 1

HCID 21220522HCID 21220522, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,4a,5,6-Tetrahydro-2-(4-methylphenyl)pyrido[3,4-h]cinnolin-3(2H)-one (0.14 g; from Example 1 above) was placed in a flask under nitrogen. Borane tetrahydofuran complex (1M, 2.4 ml) was added and the solution warmed to room temperature for 3.5 hours. Methanol (5 ml) was added. Water was added and the aqueous solution extracted thrice with ethyl acetate. The organics were washed with sodium hydrogen carbonate (saturated solution), and brine then dried, filtered and concentrated to give a yellow solid. The solid was adsorbed onto silica then chromatographed eluting with first 7:3 dichloromethane:ethyl acetate, then ethyl acetate to give a yellow solid. Recrystallisation from ethyl acetate/hexane gave the title compound (30 mg)

Workup

  1. additionBorane tetrahydofuran complex (1M, 2.4 ml) was added
  2. extractionthe aqueous solution extracted thrice with ethyl acetate
  3. washThe organics were washed with sodium hydrogen carbonate (saturated solution), and brine
  4. customthen dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. customthen chromatographed
  9. washeluting with first 7:3 dichloromethane
  10. customethyl acetate, then ethyl acetate to give a yellow solid
  11. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-de667ce73aa5428db25e3590bf0e74f4
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

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