Triethylamine → 1,2-dihydro-1-carboethoxy-2-diphenylmethyl-3H-indazol-3-one

HRID 1681687Notes

Reaction equation

HRID 1681687 reaction equation
[C:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7]1)([O:3][CH2:4][CH3:5])=[O:2].C(N(CC)CC)C.Br[CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[C:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[CH:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 236603BromodiphenylmethaneHCID 584113Ethyl 3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

Product 1

HCID 198054521,2-dihydro-1-carboethoxy-2-diphenylmethyl-3H-indazol-3-oneYield 37.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1,2-dihydro-1-carboethoxy-3H-indazol-3-one (G. Heller and P. Jacobsohn, Chem. Ber, 1921, 54B, 1107; 2.06 g), triethylamine (1.01 g) and bromodiphenylmethane (2.5 g) in chloroform (60 ml) was heated under reflux for 4 hours. The reaction mixture was then washed successively with water, M hydrochloric acid and then with water, dried (MgSO4) and evaporated. The residue was dissolved in methylene chloride and purified by column chromatography using an increasing gradient of ether in methylene chloride as eluant to give (from the later fractions) 1,2-dihydro-1-carboethoxy-2-diphenylmethyl-3H-indazol-3-one as a solid (1.4 g), m.p. 115-118° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. washThe reaction mixture was then washed successively with water, M hydrochloric acid
  4. dry with materialwith water, dried (MgSO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-c97633e1fc2e4621b1f03bd0f273c36e
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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