6-chloro-5-nitronicotinonitrile → HCID 178510357, compound

HRID 1370126Notes

Reaction equation

HRID 1370126 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1>CN(C)C=O.C(OCC)(=O)C>[OH:20][C@H:17]1[CH2:18][CH2:19][C@H:14]([NH:13][C:2]2[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 185096266-chloro-5-nitronicotinonitrileHCID 178511715HCID 178511715, compound

Product 1

HCID 178510357HCID 178510357, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-5-nitronicotinonitrile (3.5 g) in N,N-dimethylformamide (35 ml) was added trans-4-aminocyclohexanol (4.39 g) at 0° C. The mixture was stirred at ambient temperature for 45 minutes under nitrogen atmosphere, and diluted with ethyl acetate. The resultant organic solution was washed with water (3 times) and brine, dried over magnesium sulfate, and concentrated in vacuo. The residual solid was washed with diethyl ether to give 6-(trans-4-hydroxycyclohexylamino)-5-nitronicotinonitrile (3.38 g) as a yellow solid.

Workup

  1. washThe resultant organic solution was washed with water (3 times) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-7f9b1b9009df49329eb420d74fd74005
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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