Water → HCID 58009151, compound

HRID 1930401Notes

Reaction equation

HRID 1930401 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1.[CH2:14]([NH2:16])[CH3:15].O>CC#N>[Cl:13][C:4]1[CH:3]=[C:2]([NH:16][CH2:14][CH3:15])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 58009151HCID 58009151, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 4,6-dichloronicotinate (4.4 g, 20 mmol) in CH3CN (50 mL) was added dropwise a solution of ethylamine in water (65%, 2.7 g, 39 mmol) at 0° C., then the resulting mixture was stirred at RT overnight. The reaction was concentrated and the residue was washed with water to give ethyl 6-chloro-4-(ethylamino)nicotinate (3.9 g, 91% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.51 (s, 1 H), 8.08 (s, 1 H), 6.53 (m, 1 H), 4.19 (q, J=7.2 Hz, 2H), 2.78 (q, J=7.2 Hz, 2 H), 1.28 (t, J=7.2 Hz, 3 H), 1.13 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 229.1[M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. washthe residue was washed with water

Sources & evidence

ORD record
ord-a600b71f35e740ac8e51a6d9c6be6505
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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