Hydrochloric Acid → HCID 71668228, compound

HRID 508648Notes

Reaction equation

HRID 508648 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)O[C:5](=O)[C:4]=1[C:15]([O:17][CH3:18])=[O:16].[C:19]1([N:25]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][CH2:30]C3=O)=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[K+].Cl>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:30]2[CH2:29][CH2:28][C:27]3[C:32](=[CH:33][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:26]=3)[C:5]=2[C:4]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11277525HCID 11277525, compoundHCID 13792528HCID 13792528, compound

Product 1

HCID 71668228HCID 71668228, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 4-(methylthio)-2-oxo-6-(thiophen-2-yl)-2H-pyran-3-carboxylate (282 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 6 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 211 mg of (49%) of methyl 8-(methylthio)-2-phenyl-6-(thiophen-2-yl)-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-1808506593ff44bc997da7ba637629d6
Source dataset
uspto-grants-2015_08
Patent number
US09096539B2

Reaction notes

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