Hydrochloric Acid → 2-nitro-4-(1H-pyrazol-5-yl)benzonitrile

HRID 872590Notes

Reaction equation

HRID 872590 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]2[N:16](C3CCCCO3)[N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].Cl.O.[OH-].[Na+]>CCO>[N+:1]([C:4]1[CH:11]=[C:10]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 671715292-Nitro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 671687892-nitro-4-(1H-pyrazol-5-yl)benzonitrileYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-nitro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-benzonitrile (17.7 g, 59 mmol) in EtOH (440 ml) was added 44 ml of concentrated HCl. The reaction mixture was stirred at RT for 1.5 h. The mixture was poured into water (1 l), and 2 M NaOH-solution was added until pH was 12. Thus resulting precipitate was filtered, washed with water and dried to give 11.7 g (92%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.09 (d, 1H), 7.91 (d, 1H), 8.20 (d, 1H), 8.37 (dd, 1H), 8.73 (d, 1H), 13.4 (bs, 1H).

Workup

  1. additionwas added until pH was 12
  2. customThus resulting precipitate
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c7460dffb5594465aa9fda45ba62f8f3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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