Cyclohexylamine → Ethyl 5-amino-6-cyclohexylaminonicotinate

HRID 1007694Notes

Reaction equation

HRID 1007694 reaction equation
Cl[C:2]1[C:12]([N+:13]([O-])=O)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CS(C)=O.O>[NH2:13][C:12]1[C:2]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:3][CH:4]=[C:5]([CH:11]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 3784053Ethyl 6-chloro-5-nitronicotinate

Product 1

HCID 22598045Ethyl 5-amino-6-cyclohexylaminonicotinateYield 74%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Ethyl 6-chloro-5-nitronicotinate (1.00 g, 4.33 mmol) prepared according to A. H. Berrie et al. (J. Chem. Soc. 1951, 2590) was dissolved in DMSO (2 mL) and cyclohexylamine (0.54 g, 5.4 mmol) was added. The mixture was stirred for 1 h at room temperature, diluted with water and the yellow precipitated collected by filtration. The product was washed with water and dried (0.95 g, 74% yield).

Workup

  1. customthe yellow precipitated
  2. filtrationcollected by filtration
  3. washThe product was washed with water
  4. customdried (0.95 g, 74% yield)

Sources & evidence

ORD record
ord-595be4d2c0034c1ab64ed8ba11b075f4
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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