Water → HCID 86758883, compound

HRID 1862036Notes

Reaction equation

HRID 1862036 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:19](=O)[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:10]=3[NH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:24].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]([CH3:24])[C:10]3=[C:13]4[C:18](=[CH:19][C:9]=23)[CH:17]=[CH:16][CH:15]=[CH:14]4)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12972822HCID 12972822, compound

Product 1

HCID 86758883HCID 86758883, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Chlorophenyl)indeno[1,2-c]pyrazol-4(1H)-one (0.68 g) was dissolved in N,N-dimethylformamide (30 ml) under nitrogen at 20° C. Sodium hydride (106 mg, of a 60% dispersion in mineral oil) was added and the mixture was stirred for 30 minutes, then iodomethane (0.38 g) was added. The mixture was stirred at 20° C. for 2 hours and then poured into water (50 ml). A yellow solid was collected by filtration and washed with petroleum ether (25 ml). The solid was dissolved in hot ethyl acetate and pre-absorbed onto silica which was applied to the top of the silica column. The mixture was separated by flash column chromatography using dichloromethane/petroleum ether/methanol (50:50:1). Fractions were collected, combined as appropriate, and evaporated to give a solid which was crystallised from ethyl acetate to give 3-(4-chlorophenyl)-1-methylindeno [1,2-c]pyrazol-4(1H-one, m.p. 219-221° C. δH[2H6] DMSO (250 MHz) 4.07 (3H, s, NMe), 7.41 (1H, t, Ar), 7.55 (4H, m, Ar), 7.65 (1H, d, Ar-8-H), 8.13 (2H, d, Ar). The structure was identified by the presence of a Nuclear Overhauser Effect.

Workup

  1. stirringThe mixture was stirred at 20° C. for 2 hours
  2. filtrationA yellow solid was collected by filtration
  3. washwashed with petroleum ether (25 ml)
  4. dissolutionThe solid was dissolved in hot ethyl acetate
  5. custompre-absorbed onto silica which
  6. customThe mixture was separated by flash column chromatography
  7. customFractions were collected
  8. customevaporated
  9. customto give a solid which
  10. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-e6afee3dcb704b84bc8b7cbe506bb193
Source dataset
uspto-grants-2003_03
Patent number
US06534655B1

Reaction notes

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