Tetrahydrofuran → 4-Chloro-N-methyl-3-nitropyridin-2-amine

HRID 1864670Notes

Reaction equation

HRID 1864670 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:14]1COCC1>>[Cl:11][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH3:14])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 40716944-Chloro-3-nitropyridin-2-amine

Product 1

HCID 249031234-Chloro-N-methyl-3-nitropyridin-2-amineYield 25%

Conditions

Temperature
0 °C

Procedure

2-Amino-4-chloro-3-nitropyridine (590 mg, 4 mmol) was dissolved in dry THF (15 mL), the solution was cooled to 0° C. and NaH (240 mg, 6 mmol) was added. The reaction mixture was stirred for 2 hours, and allowed to warm at room temperature. The solvent was evaporated and the residue extracted between AcOEt and water. The organic layer was dried (MgSO4) and evaporated. The crude mixture was purified by column chromatography (eluent DCM) to afford the title compound (190 mg, 25%). 1H-NMR (6, ppm, DMSO-d6): 2.88 (d, 3H, Me, J=4.55 Hz), 6.86 (d, 1H, HPy,5, J=5.31 Hz), 7.44 (broad s, 1H, NH), 8.21 (d, 1H, HPy,5, J=5.30 Hz).

Workup

  1. temperatureto warm at room temperature
  2. customThe solvent was evaporated
  3. extractionthe residue extracted between AcOEt and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customThe crude mixture was purified by column chromatography (eluent DCM)

Sources & evidence

ORD record
ord-c2c06492e30a4a2eb9ed491907206444
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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