Ethyl 3-oxo-3-(pyridin-3-yl)propanoate → HCID 178426705, compound

HRID 1920043Notes

Reaction equation

HRID 1920043 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]([NH2:14])=[NH:13].O=[C:16]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:17][C:18](OCC)=[O:19]>CN1CCCC1=O.C(O)C>[OH:19][C:18]1[N:14]=[C:12]([NH:11][C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[CH3:1])[N:13]=[C:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH:17]=1

Participants

5

Reactant 2

HCID 222197Ethyl 3-oxo-3-(pyridin-3-yl)propanoateHCID 178426708HCID 178426708, compound

Product 1

HCID 178426705HCID 178426705, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

40 g (2-methyl-5-nitrophenyl)guanidine in 160 mL N-methyl pyrrolidone is dissolved. The mixture is heated to 150° C. and ethyl β-oxo-3-pyridine propionate is added portionwise, to 50 g total in a time period of 5 hours, distillating about 15 g of by-products under a nitrogen flow. At the end of the reaction, the mixture is cooled and diluted with ethanol. The precipitate is filtrated, yielding, upon drying, 46.4 g of product with HPLC purity of 99% (A %), identified through LC-MS and 1H-NMR.

Workup

  1. customAt the end of the reaction
  2. temperaturethe mixture is cooled
  3. filtrationThe precipitate is filtrated
  4. customyielding
  5. customupon drying

Sources & evidence

ORD record
ord-543f6e76df6543d6a0ebf8c8e01162ae
Source dataset
uspto-grants-2012_05
Patent number
US08168787B2

Reaction notes

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