4-Heptanamine → HCID 11391503, compound

HRID 1279261Notes

Reaction equation

HRID 1279261 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([CH:16]([NH2:20])[CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15]>CC#N>[CH3:8][C:6]1[NH:5][C:4](=[O:9])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:20][CH:16]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 386654-HeptanamineHCID 114354124-CHLORO-6-METHYL-3-NITROPYRIDIN-2(1H)-ONE

Product 1

HCID 11391503HCID 11391503, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloro-6-methyl-3-nitropyridone (2.9 g, 15.40 mmol) was treated with 1-propylbutylamine (4 mL, 26.8 mmol) in CH3CN (30 mL) at 25° C. for 64 h and at reflux for 2 h. The reaction mixture was partitioned between EtOAc (200 mL) and water (50 mL). The EtOAc was washed with water (2×50 mL), brine, dried (MgSO4) and stripped in vacuo. The residue was washed with 20% EtOAc/hexanes (2×20 mL) to give the product (3.7 g).

Workup

  1. temperatureat reflux for 2 h
  2. customThe reaction mixture was partitioned between EtOAc (200 mL) and water (50 mL)
  3. washThe EtOAc was washed with water (2×50 mL), brine
  4. dry with materialdried (MgSO4)
  5. washThe residue was washed with 20% EtOAc/hexanes (2×20 mL)

Sources & evidence

ORD record
ord-a185a019c3294c18a7579d225bb6b6f4
Source dataset
uspto-grants-2002_09
Patent number
US06448261B1

Reaction notes

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