Hydrochloric Acid → 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile

HRID 872612Notes

Reaction equation

HRID 872612 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[N:14](C3CCCCO3)[N:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:21])[C:3]=1[C:4]#[N:5].Cl.CCO.C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:21])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 671718412-Chloro-6-fluoro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 671697812-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrileYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-6-fluoro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile (1.09 g, 3.55 mmol) was stirred with 10% HCl (g)/EtOH-solution (50 ml) at room temperature for 1 h. Reaction mixture was poured into water (50 ml) and made slightly alkaline with saturated NaHCO3 solution. Thus resulting precipitate was filtered, washed with water and dried in vacuum to obtain 0.74 g (94%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.06 (d, 1H), 7.94 (dd, 1H), 8.05 (m, 1H), 13.4 (bs, 1H).

Workup

  1. customReaction mixture
  2. customThus resulting precipitate
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-f5e703e5e5c6441092fcaf1b68f22b0a
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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