m-Chloroperbenzoic acid → HCID 178507188, compound

HRID 931397Notes

Reaction equation

HRID 931397 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1>CC(C)=O>[NH2:19][C:14]1[C:13]([Br:12])=[CH:18][CH:17]=[CH:16][N+:15]=1[O-:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 178507188HCID 178507188, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
23 °C

Procedure

mCPBA (12.0 g, 69.3 mmol) was added portionwise over 5 min to a solution of 3-bromopyridin-2-amine (10 g, 58 mmol) in anhydrous acetone (150 mL) at 0° C. The resulting mixture was warmed to 23° C. and stirred for 1 h, then concentrated. The residue was partitioned between a solution of 5% methanol in chloroform and saturated aqueous sodium hydroxide solution (3×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound. MS: m/z=189.0 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between a solution of 5% methanol in chloroform and saturated aqueous sodium hydroxide solution (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0af1ba88a13c40cf9271a89f2638e8d5
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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