Ethanol → HCID 67273917, compound

HRID 598218Notes

Reaction equation

HRID 598218 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][NH2:22].[CH2:25](O)[CH3:26]>>[CH3:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][NH:22][C:2]1[C:3]([C:4]([O:6][CH2:25][CH3:26])=[O:5])=[CH:7][CH:8]=[C:9]([CH3:11])[N:10]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 197093,3-DimethylbutylamineHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 67273917HCID 67273917, compound

Conditions

Temperature
160 °C

Procedure

A solution of 2-chloro-6-methylnicotinic acid (0.500 g, 2.91 mmol) in ethanol (5.0 mL) was treated with potassium carbonate (0.810 g, 5.80 mmol) followed by (3,3-dimethylbutyl)amine (0.590 mL, 4.35 mmol). The mixture was stirred at reflux for 3 h and then heated to 160° C. for 1 h in a Biotage Initiator microwave synthesizer. A solid was decanted and the mother liquor was further diluted with ethanol (5.0 mL) and treated with concentrated sulfuric acid (3.0 mL). The solution was then refluxed overnight, cooled to ambient temperature, and neutralized to pH ˜7 using 6N aqueous sodium hydroxide. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic portions were dried over magnesium sulfate, filtered, and concentrated in vacuo. The title compound was obtained as a clear oil (0.578 g, 75%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.99 (d, J=7.8 Hz, 1H), 7.84 (br. s., 1H), 6.35 (d, J=7.8 Hz, 1H), 4.30 (q, J=7.2 Hz, 2H), 3.44-3.58 (m, 2H), 2.92-3.05 (m, 2H), 2.42 (s, 3H), 1.37 (t, J=7.2 Hz, 3H), 0.99 (s, 9H). MS(ES+) m/e 265 [M+H]+.

Workup

  1. temperatureat reflux for 3 h
  2. customA solid was decanted
  3. additionthe mother liquor was further diluted with ethanol (5.0 mL)
  4. additiontreated with concentrated sulfuric acid (3.0 mL)
  5. temperatureThe solution was then refluxed overnight
  6. temperaturecooled to ambient temperature
  7. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  8. dry with materialThe combined organic portions were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9fe95e1848c4578a7e08d77b66c151d
Source dataset
uspto-grants-2011_03
Patent number
US07897612B2

Reaction notes

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