N-bromobutanimide → HCID 86755097, compound

HRID 376431Notes

Reaction equation

HRID 376431 reaction equation
[CH3:1][C:2]1([C:13]([OH:15])=[O:14])[CH:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[NH:3]1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([C:13]([OH:15])=[O:14])[CH:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Br:16])[N:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68808373HCID 68808373, compound

Product 1

HCID 86755097HCID 86755097, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-methyl-1-(pyridin-2-yl)-1H-pyrazolecarboxylic acid (7.0483 mmol, 1.63 g) and N-bromosuccinimide (2.51 g, 2.0 eq.) in carbon tetrachloride (40 mL) was stirred at ambient temperature for 18 h. The reaction mixture was filtered through celite to remove solid impurity and washed with carbon tetrachloride (30 mL). The filtrate was evaporated and purified by flash chromatography on a silica gel column (200 g) eluted with 3:1 hexane:ethyl acetate to give 0.258 g of pure 3-methyl-1-(6-bromopyridin-2-yl)-1H-pyrazolecarboxylic acid (12%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customto remove solid impurity
  3. washwashed with carbon tetrachloride (30 mL)
  4. customThe filtrate was evaporated
  5. custompurified by flash chromatography on a silica gel column (200 g)
  6. washeluted with 3:1 hexane

Sources & evidence

ORD record
ord-23b8b13e329247ec8313b4002cedbb5a
Source dataset
uspto-grants-2000_02
Patent number
US06020357

Reaction notes

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