Hydrogen Bromide → HCID 18676088, compound

HRID 1635491Notes

Reaction equation

HRID 1635491 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=3)[N:12]=[C:11]([CH3:21])[CH:10]=2)[CH:6]=[CH:5][N:4]=1.Br.O.[OH-].[NH4+]>C(O)(=O)C>[CH3:20][C:16]1[CH:15]=[C:14]([N:13]2[C:9]([C:7]3[CH:6]=[CH:5][NH:4][C:3](=[O:2])[CH:8]=3)=[CH:10][C:11]([CH3:21])=[N:12]2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14923Ammonium HydroxideHCID 9795661HCID 9795661, compound

Product 1

HCID 18676088HCID 18676088, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-methoxy-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 22; 0.56 g, 0.002 mol) in 5 mL of acetic acid was added 5 mL of hydrobromic acid. The reaction mixture was heated at reflux for 3 hours and then cooled to room temperature. Water was added and the solution was basified with ammonium hydroxide. The aqueous phase was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 0.45 g (85%) of product as a white solid: mp: 182-183° C.; Anal. Calc'd. for C16H15N3O: C, 72.43; H, 5.70; N, 15.84. Found: C, 72.37; H, 5.66; N, 15.97.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-123e258b8173493cb1dfad4cc4025ab2
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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