Pyridinium chloride → 6-chloro-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

HRID 2076363Notes

Reaction equation

HRID 2076363 reaction equation
C([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:24]4[C:18]5([CH2:27][CH:21]([C:22](=[O:26])[C:23]=4[Cl:25])[CH2:20][CH2:19]5)[CH2:17][C:14]=32)=[N:9]1)C1C=CC=CC=1.Cl.N1C=CC=CC=1>>[Cl:25][C:23]1[C:22](=[O:26])[CH:21]2[CH2:27][C:18]3([C:24]=1[C:13]1[CH:12]=[CH:11][C:10]4[NH:9][N:8]=[CH:16][C:15]=4[C:14]=1[CH2:17]3)[CH2:19][CH2:20]2

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 593972242-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

Product 1

HCID 593972266-chloro-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

Conditions

Temperature
195 °C

Procedure

A mixture of 2-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a -methanoazuleno[2,1-e]indazol-7(8H)-one (0.622 g, 1.66 mmol) and pyridine hydrochloride (10 g, 87 mmol) was heated to 195° C. After 2.5 hours the reaction mixture was allowed to cool to room temperature and was partitioned between EtOAc and water. The organic phase was washed successively with water (3×), 1N aqueous HCl, water and brine and dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel (elution with 15:85 to 80:20 EtOAc/hexanes) to yield 6-chloro-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a solid.

Workup

  1. temperatureto cool to room temperature
  2. customwas partitioned between EtOAc and water
  3. washThe organic phase was washed successively with water (3×), 1N aqueous HCl, water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was chromatographed on silica gel (elution with 15:85 to 80:20 EtOAc/hexanes)

Sources & evidence

ORD record
ord-166db5001dfa46ee800b88098624a909
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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