Cyclohexylamine → Ethyl 5-amino-6-cyclohexylaminonicotinate

HRID 1018253Notes

Reaction equation

HRID 1018253 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-694c133544054993a29feea37ed77e29
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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