Bromine → HCID 21220554, compound

HRID 1584734Notes

Reaction equation

HRID 1584734 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[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.BrBr.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[CH:16]=[C: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

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 21220552HCID 21220552, compound

Product 1

HCID 21220554HCID 21220554, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

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 dissolved in acetic acid (2 ml) and heated to 80° C. Bromine (0.027 ml) was added dropwise and the solution stirred for 16 hours. The reaction was cooled to room temperature, poured into aqueous sodium hydrogen carbonate and extracted thrice with dichloromethane. The organics were washed with sodium thiosulphate solution and brine, dried, filtered and concentrated. The product was adsorbed onto silica then chromatographed eluting with 1:1 dichloromethane:ethyl acetate then recrystallised from isopropanol twice to give the title compound (35 mg).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted thrice with dichloromethane
  3. washThe organics were washed with sodium thiosulphate solution and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthen chromatographed
  8. washeluting with 1:1 dichloromethane
  9. customethyl acetate then recrystallised from isopropanol twice

Sources & evidence

ORD record
ord-5df062997af54bc1b29bcdebd82bb21b
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

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