Bromine → HCID 91032561, compound

HRID 1357258Notes

Reaction equation

HRID 1357258 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][N:13]([CH3:30])[C:14]([C:16]1[CH:17]=[N:18][N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20]=1[CH2:21][CH2:22][CH3:23])=[O:15])[CH:6]=[CH:5]2.[Br:31]Br>C(O)(=O)C>[Br:31][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH2:12][N:13]([CH3:30])[C:14]([C:16]1[CH:17]=[N:18][N:19]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:20]=1[CH2:21][CH2:22][CH3:23])=[O:15])=[CH:8]2

Participants

4

Reactant 2

HCID 24408BromineHCID 131723967HCID 131723967, compound

Product 1

HCID 91032561HCID 91032561, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-Phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (6-hydroxy-naphthalen-2ylmethyl)-methyl-amide (3.2 g, 8 mmol), prepared in the previous step, was dissolved in 300 mL glacial acetic acid (with warming). A solution of bromine (0.41 mL, 8 mmol) in 50 mL of glacial acetic acid was added under nitrogen dropwise over 2 h to the reaction at room temperature. After the addition the reaction stirred for 2 days. The solvent was removed under reduced pressure and the residue diluted with methylene chloride. The organic layer was extracted two times with 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure to give 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (3.77 g, 98.5%) as a pink solid, mp 205-207° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue diluted with methylene chloride
  4. extractionThe organic layer was extracted two times with 5% NaHCO3
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a297327696704be694cc8fca5ae3bed9
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…