2-Chloro-6-diethylamino-isonicotinic acid ethyl ester → HCID 67026884, compound

HRID 2047269Notes

Reaction equation

HRID 2047269 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[N:8]=[C:7](Cl)[CH:6]=1)[CH3:2].[CH3:18][Zn]Cl>O1CCOCC1.O>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:6]=[C:7]([CH3:18])[N:8]=[C:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 866405932-Chloro-6-diethylamino-isonicotinic acid ethyl esterHCID 178477798HCID 178477798, compound

Product 1

HCID 67026884HCID 67026884, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-chloro-6-diethylamino-isonicotinic acid ethyl ester (10.1 g, 31.6 mmol) in dioxane (120 mL), Pd(dppf) (262 mg, 0.322 mmol) is added. MeZnCl (8.40 g, 72.4 mmol) is added dropwise to the mixture before it is stirred at 75° C. for 18 h. The mixture is carefully diluted with water, then extracted with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-diethylamino-6-methyl-isonicotinic acid ethyl ester (6.39 g, containing some methyl ester) as a pale yellow oil; LC-MS: tR=0.70 min, [M+H]+=237.11.

Workup

  1. extractionextracted with EA
  2. dry with materialextracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-be79065048e14afeaeb415ca0dd07c8a
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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