Hydrochloric Acid → HCID 71668225, compound

HRID 508644Notes

Reaction equation

HRID 508644 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2O[C:13](=O)[C:12]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([S:20][CH3:21])[CH:10]=2)=[CH:5][CH:4]=1.[C:22]1([N:28]2[CH:36]=[C:35]3[C:30]([CH2:31][CH2:32][CH2:33]C3=O)=[N:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[K+].Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:33]3[CH2:32][CH2:31][C:30]4[C:35](=[CH:36][N:28]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:29]=4)[C:13]=3[C:12]([C:16]([O:18][CH3:19])=[O:17])=[C:11]([S:20][CH3:21])[CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12342085HCID 12342085, compoundHCID 13792528HCID 13792528, compound

Product 1

HCID 71668225HCID 71668225, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 6-(4-methoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carboxylate (306 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 8 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 269 mg (59%) of methyl 6-(4-methoxyphenyl)-8-(methylthio)-2-phenyl-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-6baa7ece90554b498ea0d6d430a00e0c
Source dataset
uspto-grants-2015_08
Patent number
US09096539B2

Reaction notes

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