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

HRID 1370102Notes

Reaction equation

HRID 1370102 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]#[N:12])=[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>[C:11]([C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)=[N:3][CH:4]=1)#[N:12]

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 2-chloro-5-cyano-3-nitropyridine (3.5 g)(obtained according to International Patent Application No.WO9410171) in N,N-dimethylformamide (35 mL) was added trans-4-aminocyclohexanol (4.39 g) at 0° C. The mixture was stirred at room temperature under nitrogen atmosphere for 45 minutes and diluted with ethyl acetate. The mixture was washed with water (3 times) and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual solid was washed with diethyl ether to give 5-cyano-2-(trans-4-hydroxycyclohexylamino)-3-nitropyridine (3.38 g) as a yellow sold.

Workup

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

Sources & evidence

ORD record
ord-366e512f3b034dd2bdc55c2b45d9182c
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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