Cyclohexylamine → Ethyl 5-amino-6-cyclohexylaminonicotinate

HRID 1280077Notes

Reaction equation

HRID 1280077 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-c0706c135a554850aa3abdbad98c3f74
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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