Isopropylamine → 2-bromo-N-isopropyl-5-nitropyridin-4-amine

HRID 1778025Notes

Reaction equation

HRID 1778025 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[Br:5][C:6]1[CH:11]=[C:10](Br)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][N:7]=1>C1COCC1.O>[Br:5][C:6]1[CH:11]=[C:10]([NH:4][CH:1]([CH3:3])[CH3:2])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 160998502,4-Dibromo-5-nitropyridine

Product 1

HCID 901766982-bromo-N-isopropyl-5-nitropyridin-4-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of isopropylamine (17 ml, 34.0 mmol) in THF (14 ml) was added dropwise over 1 h to a mixture of 2,4-dibromo-5-nitropyridine (4.94 g, 17.0 mmol) in THF (85 ml) at room temperature. After 5.5 h, the reaction mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and evaporated to give the crude title compound as a yellow solid. (UPLC-MS 6) tR 1.03; ESI-MS 260.0/262.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-e8d4f605efee425e8786c56e8325d032
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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