Methane → HCID 178509585, compound

HRID 1409402Notes

Reaction equation

HRID 1409402 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[NH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].C.[OH-].[Na+]>CO>[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][NH:14][N:15]=2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 671717272-Chloro-4-(1H-pyrazol-3-yl)benzonitrile hydrochloride

Product 1

HCID 178509585HCID 178509585, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride (8 g, 33.3 mmol) was charged to the reaction flask and methanol (74 ml), activated charcoal (0.36 g) and celite (0.46 g) were added. The reaction mixture was refluxed for 1 h, filtered, and the solid was washed with warm methanol. A half of the methanol was distilled out and water (40 ml) was added at 55° C. slowly. 50% NaOH solution (1.916 ml, 36.7 mmol) was added slowly, the mixture was stirred for 10 min and cooled to RT. MeOH was evaporated and residue cooled to RT. Water (49 ml) was added and the precipitate was filtered and washed with water and dried under vacuum overnight at 60° C. to obtain 6.21 g of the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 6.99 (d, 1H), 7.86 (d, 1H), 7.96-8.01 (m, 2H), 8.24-8.16 (m, 1H).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. filtrationfiltered
  4. washthe solid was washed with warm methanol
  5. distillationA half of the methanol was distilled out and water (40 ml)
  6. additionwas added at 55° C. slowly
  7. customMeOH was evaporated
  8. temperatureresidue cooled to RT
  9. additionWater (49 ml) was added
  10. filtrationthe precipitate was filtered
  11. washwashed with water
  12. customdried under vacuum overnight at 60° C.

Sources & evidence

ORD record
ord-1afca112db74479fadbc57f593c9da04
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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