Chlorosuccinimide → 3-Chloro-5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one

HRID 1639255Notes

Reaction equation

HRID 1639255 reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5](=[O:12])[C:4]2=[CH:13][CH:14]=[CH:15][N:3]12.[Cl:16]N1C(=O)CCC1=O>O1CCCC1>[Cl:16][C:15]1[N:3]2[N:2]([CH3:1])[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5](=[O:12])[C:4]2=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 141715685-methylpyrrolo[1,2-b]cinnolin-10(5H)-one

Product 1

HCID 141715713-Chloro-5-methylpyrrolo[1,2-b]cinnolin-10(5H)-oneYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one (5.0 g) in 180 mL of tetrahydrofuran at 0° C. was treated with N-chlorosuccinimide (3.4 g) all at once and the mixture was stirred at ambient temperature. After 36 h the solution was concentrated and the residue taken up in chloroform. This solution was washed with two 100 ml portions of water, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica, dichloromethane) to give 2.83 g of an off-white powder, mp 88.5°-90.5° C.

Workup

  1. concentrationAfter 36 h the solution was concentrated
  2. washThis solution was washed with two 100 ml portions of water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-fd3922e11c134d1ea072485aa60ff43c
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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