Hydrochloric Acid → HCID 71668224, compound

HRID 508643Notes

Reaction equation

HRID 508643 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2O[C:12](=O)[C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([S:19][CH3:20])[CH:9]=2)=[CH:4][CH:3]=1.[C:21]1([N:27]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][CH2:32]C3=O)=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[K+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:32]3[CH2:31][CH2:30][C:29]4[C:34](=[CH:35][N:27]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:28]=4)[C:12]=3[C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([S:19][CH3:20])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11758732HCID 11758732, compoundHCID 13792528HCID 13792528, compound

Product 1

HCID 71668224HCID 71668224, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 6-(4-chlorophenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carboxylate (330 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 267 mg (58%) of methyl 6-(4-chlorophenyl)-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-0158b8842c814cdca32e9cb0e813ad74
Source dataset
uspto-grants-2015_08
Patent number
US09096539B2

Reaction notes

Loading…