Phosphorus tribromide → HCID 21186713, compound

HRID 1384270Notes

Reaction equation

HRID 1384270 reaction equation
P(Br)(Br)Br.[CH3:5][C:6]1[N+:11]([O-])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[C:8]([N+:18]([O-:20])=[O:19])[C:7]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:5][C:6]1[N:11]=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[C:8]([N+:18]([O-:20])=[O:19])[C:7]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 70224229HCID 70224229, compound

Product 1

HCID 21186713HCID 21186713, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Phosphorus tribromide (3.51 g, 12.5 mmol) was dissolved in ethyl acetate (12.0 ml) to which was subsequently added dropwise ethyl acetate solution (10.0 ml) of ethyl 2-methyl-4-nitro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (1.47 g, 5.00 mmol) at room temperature, and the resulting mixture was stirred at the same temperature for 10 minutes and then at 80° C. for 15 minutes. After cooling, the reaction solution was poured into ice water, mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1) to obtain the title compound (1.36 g, 97.9%) as pale brown oil.

Workup

  1. waitat 80° C. for 15 minutes
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washthe thus obtained organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-e14dc67c077d430385b4e83dd7a7eccd
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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