Hydrochloric Acid → HCID 71668226, compound

HRID 508645Notes

Reaction equation

HRID 508645 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)O[C:5](=O)[C:4]=1[C:16]([O:18][CH3:19])=[O:17].[C:20]1([N:26]2[CH:34]=[C:33]3[C:28]([CH2:29][CH2:30][CH2:31]C3=O)=[N:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[K+].Cl>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:31]2[CH2:30][CH2:29][C:28]3[C:33](=[CH:34][N:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:27]=3)[C:5]=2[C:4]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13792528HCID 13792528, compoundHCID 14000272HCID 14000272, compound

Product 1

HCID 71668226HCID 71668226, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 4-(methylthio)-2-oxo-6-phenyl-2H-pyran-3-carboxylate (276 mg, 1 mmol), 2-phenyl-6,7-dihydro-2H-indazol-4(5H)-one (212 mg, 1 mmol) and powdered KOH (84 mg, 1.5 mmol) in dry DMF (5 mL) was stirred at 25° C. for 7 hr. At the end the reaction mixture was poured into ice water with vigorous stirring and finally neutralized with dilute HCl. The solid thus obtained was filtered and purified on a neutral alumina column using 15% chloroform in hexane as eluent to yield 234 mg (55%) of methyl 8-(methylthio)-2,6-diphenyl-4,5-dihydro-2H-benzo[e]indazole-9-carboxylate.

Workup

  1. stirringwith vigorous stirring
  2. customThe solid thus obtained
  3. filtrationwas filtered
  4. custompurified on a neutral alumina column

Sources & evidence

ORD record
ord-cad45574398a45bb9d8eb9ba8062da7e
Source dataset
uspto-grants-2015_08
Patent number
US09096539B2

Reaction notes

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