Hydrochloric Acid → 6,7-Dihydro-2H-benzo[6,7]cyclohepta[cd]indazole-8-carboxylic acid

HRID 132994Notes

Reaction equation

HRID 132994 reaction equation
[N:1]1[NH:2][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]3[CH2:13][CH2:12][C:11]4=[C:14]([CH:18]=[O:19])[CH:15]=[CH:16][CH:17]=[C:10]4[C:9]=1[C:8]=23.P([O-])(O)(O)=[O:21].[Na+].Cl[O-].[Na+].Cl>CS(C)=O.O>[N:1]1[NH:2][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]3[CH2:13][CH2:12][C:11]4=[C:14]([C:18]([OH:21])=[O:19])[CH:15]=[CH:16][CH:17]=[C:10]4[C:9]=1[C:8]=23

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 102145986,7-Dihydro-2H-benzo[6,7]cyclohepta[cd]indazole-8-carboxaldehydeHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphate

Product 1

HCID 102146696,7-Dihydro-2H-benzo[6,7]cyclohepta[cd]indazole-8-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

85 mg of 6,7-dihydro-2H-benzo[6,7]cyclohepta[cd]indazole-8-carboxaldehyde prepared in Example 2 was dissolved in 8 ml of dimethyl sulfoxide. To the reaction mixture was added a solution of 0.75 g of sodium dihydrogenphosphate in 4 ml water. Further, a solution of 0.25 g of sodium hypochlorite in 1 ml water was added dropwise at room temperature, followed by stirring for 0.5 hour. To the reaction mixture was added 0.01 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:1), to give 85 mg of the title compound as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-5582d8cff1624cd699e9d42af041967f
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

Loading…