Chlorosuccinimide → 2-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

HRID 2076362Notes

Reaction equation

HRID 2076362 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:24]4[C:18]5([CH2:26][CH:21]([C:22](=[O:25])[CH:23]=4)[CH2:20][CH2:19]5)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:24]4[C:18]5([CH2:26][CH:21]([C:22](=[O:25])[C:23]=4[Cl:27])[CH2:20][CH2:19]5)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 59397235HCID 59397235, compound

Product 1

HCID 593972242-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-benzyl-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one (0.737 g, 2.17 mmol) in 15 mL of dimethylformamide was heated to 60° C. and N-chlorosuccinimide (0.290 g, 2.17 mmol) was added. After heating for 45 minutes, additional N -chlorosuccinimide (0.074 g, 0.55 mmol) was added. After heating for 55 minutes more, the reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel (elution with 15:85 to 80:20 EtOAc/hexanes) to yield 2-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a white solid.

Workup

  1. temperatureAfter heating for 45 minutes
  2. temperatureAfter heating for 55 minutes more
  3. custompartitioned between EtOAc and water
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica gel (elution with 15:85 to 80:20 EtOAc/hexanes)

Sources & evidence

ORD record
ord-84c67e4856b34b1d8a6519ae41fb982d
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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