2-Ethyl butylamine → Ethyl 2-[(2-ethylbutyl)amino]nicotinate

HRID 601100Notes

Reaction equation

HRID 601100 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][NH2:17])[CH3:14]>>[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][NH:17][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:14]

Participants

3

Reactant 2

HCID 120492-Ethyl butylamineHCID 2796614Ethyl chloronicotinate

Product 1

HCID 67064133Ethyl 2-[(2-ethylbutyl)amino]nicotinateYield 76.3%

Procedure

Ethyl 2-chloronicotinate (0.646 g, 3.48 mmol) and 2-ethylbutylamine (0.74 g, 7.31 mmol) were reacted in a sealed tube at 130° C. for 2 hours. The reaction mixture was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane (2×50 mL). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (19:1) to provide the title compound (0.665 g, 76%). MS (ESI+) m/z 251.1 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 0.93 (t, J=7.54 Hz, 6H), 1.41 (m, 7H), 1.55 (m, 1H), 3.46 (m, 2H), 4.32 (q, J=6.99 Hz, 2H), 6.48 (dd, J=7.72, 4.78 Hz, 1H), 7.99 (s, 1H), 8.11 (dd, J=7.72, 2.21 Hz, 1H), 8.27 (dd, J=4.78, 1.84 Hz, 1H).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (19:1)

Sources & evidence

ORD record
ord-a52b3c6cb8004d38a07d829b9ddf46ec
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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