Chlorosuccinimide → HCID 14371424, compound

HRID 2291991Notes

Reaction equation

HRID 2291991 reaction equation
[CH2:1]([N:8]1[C:17]2[CH:16]=[C:15]([Cl:18])[CH:14]=[CH:13][C:12]=2[C:11](=[O:19])[C:10]2=[CH:20][CH:21]=[CH:22][N:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23]N1C(=O)CCC1=O.[Al]>C1COCC1>[CH2:1]([N:8]1[C:17]2[CH:16]=[C:15]([Cl:18])[CH:14]=[CH:13][C:12]=2[C:11](=[O:19])[C:10]2=[CH:20][CH:21]=[C:22]([Cl:23])[N:9]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 5359268AluminumHCID 14171579HCID 14171579, compound

Product 1

HCID 14371424HCID 14371424, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyl-7-chloropyrrolo[1,2-b]cinnolin-10(5H)-one (4.5 g) was taken up in 50 ml of THF and a catalytic amount of dibenzoyl eroxide was added. N-chlorosuccinimide (1.95 g) was added portionwise over a period of 10 min. The flask was covered with aluminum foil and the mixture stirred at room temperature overnight under N2. The reaction mixture was concentrated and the residue taken up in chloroform and extracted with H2O and brine. The organic layer was then dried (MgSO4), charcoaled, filtered and concentrated to a green semisolid. This was purified by HPLC (silica, dichloromethane) to give a light green powder which was recrystallized from ethanol to yield 2.3 g of green crystals, mp 134°-136°.

Workup

  1. additiona catalytic amount of dibenzoyl eroxide was added
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with H2O and brine
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a green semisolid
  7. customThis was purified by HPLC (silica, dichloromethane)
  8. customto give a light green powder which
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-8062390645fb4dc79d94c52770730f99
Source dataset
uspto-grants-1989_01
Patent number
US04800203

Reaction notes

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