Ethanol → HCID 57907648, compound

HRID 1968448Notes

Reaction equation

HRID 1968448 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([O:13]CC)=O)=[N:6][CH:7]=1.C(O)C.O.[NH2:21][NH2:22]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:13])[NH:21][N:22]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 57907663Ethyl 4-(5-chloropyridin-2-yl)-4-oxobutanoate

Product 1

HCID 57907648HCID 57907648, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dry 200 mL flask equipped with magnetic stirrer, and reflux condenser was charged 3.7 g ethyl 4-(5-chloropyridin-2-yl)-4-oxobutanoate (0.0153 mol), 75 mL ethanol, and 0.8 g of hydrazine hydrate (0.0168 mol). The reaction was heated at reflux for about 2 hours. An aliquot was analyzed by GC which indicated no remaining starting material, and one major product. The reaction was cooled and poured into about 200 mL of water to afford a tan solid which was collected by vacuum filtration, washed with water, hexane, and dried overnight in vacuo at 40° C. Isolated 2.6 g of a tan solid. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 2.65 (t, 2H); 3.22 (t, 2H), 7.75 (d, 1H); 8.00 (d, 1H); 8.60 (s, 1H); 8.70 (bs, 1H). The sample was stored in the refrigerator and had 81% isolated yield.

Workup

  1. customTo a dry 200 mL flask equipped with magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction was heated
  4. temperatureat reflux for about 2 hours
  5. temperatureThe reaction was cooled
  6. customto afford a tan solid which
  7. filtrationwas collected by vacuum filtration
  8. washwashed with water, hexane
  9. customdried overnight in vacuo at 40° C

Sources & evidence

ORD record
ord-9d3027063389452d8ae444f0bf1c8a99
Source dataset
uspto-grants-2013_04
Patent number
US08426412B2

Reaction notes

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