Cyclohexylamine → Ethyl 5-amino-6-cyclohexylaminonicotinate

HRID 1760272Notes

Reaction equation

HRID 1760272 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 precipitate collected by filtration. The product was washed with water and dried (0.95 g, 74% yield).

Workup

  1. filtrationthe yellow precipitate collected by filtration
  2. washThe product was washed with water
  3. customdried (0.95 g, 74% yield)

Sources & evidence

ORD record
ord-e1e930e1f67d41cfb65e936e1c86166c
Source dataset
uspto-grants-2005_01
Patent number
US06841566B2

Reaction notes

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