Diethylamine → HCID 66935459, compound

HRID 1908793Notes

Reaction equation

HRID 1908793 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([N:16]([CH2:17][CH3:18])[CH2:14][CH3:15])=[N:7][CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 66935459HCID 66935459, compoundYield 86.1%

Conditions

Temperature
80 °C

Procedure

A mixture of 5,6-dichloronicotinic acid ethyl ester (2.91 g, 15.2 mmol) and diethyl-amine (11.1 g, 152 mmol) is stirred in a sealed vessel at 80° C. for 72 h. The mixture is cooled to rt and concentrated. The residue is dissolved in DCM (15 mL) and washed with 1 N aq. KHSO4 solution (2×50 mL). The washings are extracted back with DCM (50 mL). The combined org. extracts are dried over Na2SO4, filtered, concentrated and dried to give 5-chloro-6-diethylamino-nicotinic acid ethyl ester (3.36 g) as a yellow oil; LC-MS: tR=1.08 min, [M+1]+=257.12; 1H NMR (CDCl3): δ 1.26 (t, J=7.0 Hz, 6H), 1.39 (t, J=7.3 Hz, 3H), 3.62 (q, J=7.0 Hz, 4H), 4.36 (q, J=7.3 Hz, 2H), 8.07 (s, 1H), 8.70 (s, 1H).

Workup

  1. temperatureThe mixture is cooled to rt
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in DCM (15 mL)
  4. washwashed with 1 N aq. KHSO4 solution (2×50 mL)
  5. extractionThe washings are extracted back with DCM (50 mL)
  6. dry with materialextracts are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

Sources & evidence

ORD record
ord-c431c85a5d0143989f7ffbc3b33d6953
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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