Sodium Nitrite → HCID 178481732, compound

HRID 588630Notes

Reaction equation

HRID 588630 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14](=[O:16])[CH3:15].[N:17]([O-])=O.[Na+]>[CH]Cl.O>[CH3:7][N:6]1[C:2]2[N:1]=[N:17][CH:15]=[C:14]([OH:16])[C:3]=2[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5]1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 45275253HCID 45275253, compound

Product 1

HCID 178481732HCID 178481732, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6432229CID 6432229Solvent

Conditions

Temperature
-5 °C

Procedure

A suspension of 1-(5-amino-1-methyl-3-phenyl-pyrazol-4-yl)ethanone (241 mg, 1.12 mmol) in cHCl (6.7 mL) and water (1 mL) was cooled to −5° C. A solution of sodium nitrite (155 mg, 2.24 mmol) in water (0.6 mL) was added and the reaction mixture was stirred at −5° C. for 20 min, then at room temperature for 10 min, then at 65° C. for 30 min and finally cooled to room temperature. The reaction mixture was filtered and the solid was washed with cHCl (2 mL), suspended in MeOH/CH2Cl2 (9:1), filtered and dried, to yield the title compound as a solid (125 mg).

Workup

  1. waitat room temperature for 10 min
  2. waitat 65° C. for 30 min
  3. temperaturefinally cooled to room temperature
  4. filtrationThe reaction mixture was filtered
  5. washthe solid was washed with cHCl (2 mL)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-045027105e60480d93bbcafe4e7d677a
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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