Cyclopropylamine → 2-Bromo-5-(cyclopropylamino)-4-nitropyridine 1-oxide

HRID 2209034Notes

Reaction equation

HRID 2209034 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][N+:3]=1[O-:12].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:16][CH:13]2[CH2:15][CH2:14]2)=[CH:4][N+:3]=1[O-:12]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 707008042-Bromo-5-fluoro-4-nitropyridine 1-oxide

Product 1

HCID 1178439982-Bromo-5-(cyclopropylamino)-4-nitropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-fluoro-4-nitropyridine 1-oxide (3000 mg, 12.66 mmol) in THF (10 mL) was added cyclopropylamine (868 mg, 15.1 mmol). Solution was stirred at room temperature for 1 h. Mixture was partitioned between EtOAc and saturated aqueous NaHCO3. Organic layer was washed with brine and dried over MgSO4 to provide 2-bromo-5-(cyclopropylamino)-4-nitropyridine 1-oxide 2.67. Residue was used for next step without further purification. LC/MS found for C8H8BrN3O3 as (M+H)+ 275.9.

Workup

  1. customMixture was partitioned between EtOAc and saturated aqueous NaHCO3
  2. washOrganic layer was washed with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-cb5b189950994fd185876f5bea982ccf
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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