Hydrochloric Acid → HCID 71668227, compound

HRID 508647Notes

Reaction equation

HRID 508647 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)OC(=O)[C:4]=1[C:20]([O:22][CH3:23])=[O:21].[C:24]1([N:30]2[CH:38]=[C:37]3[C:32]([CH2:33][CH2:34][CH2:35][C:36]3=O)=[N:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[K+].Cl>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:35]2[CH2:34][CH2:33][C:32]3[C:37](=[CH:38][N:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:31]=3)[C:36]=2[C:4]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11001926HCID 11001926, compoundHCID 13792528HCID 13792528, compound

Product 1

HCID 71668227HCID 71668227, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 4-(methylthio)-6-(naphthalen-1-yl)-2-oxo-2H-pyran-3-carboxylate (326 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 stifling 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 228 mg (48%) of methyl 8-(methylthio)-6-(naphthalen-1-yl)-2-phenyl-4,5-dihydro-2H-benzo[e]indazole-9-carboxylate.

Workup

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

Sources & evidence

ORD record
ord-a8d401342aea4a959523844be4eabff3
Source dataset
uspto-grants-2015_08
Patent number
US09096539B2

Reaction notes

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