Isoamylamine → HCID 22349345, compound

HRID 896297Notes

Reaction equation

HRID 896297 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([NH2:18])[CH2:14][CH:15]([CH3:17])[CH3:16]>CN(C=O)C>[CH3:16][CH:15]([CH3:17])[CH2:14][CH2:13][NH:18][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 22349345HCID 22349345, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-3-nitrobenzonitrile (18.3 g, 0.10 mol) and isoamylamine (19.2 g, 0.22 mol) in DMF (250 mL) was heated to 90° C. for 4 h under nitrogen then cooled and the solvent evaporated. The residue is triturated with EtOAc (300 mL) and solids removed by filtration. The filtrate was washed with water and brine. The organic layer was dried over MgSO4 and evaporated. The residue was recrystallized from MeOH to give 21.0 g (90%) of 4-(3-methyl-butylamino)-3-nitro-benzonitrile as a yellow crystalline solid.

Workup

  1. temperaturethen cooled
  2. customthe solvent evaporated
  3. customThe residue is triturated with EtOAc (300 mL) and solids
  4. customremoved by filtration
  5. washThe filtrate was washed with water and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-f5826d8c5c454360923566cdcc24b79f
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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