Pyridine → HCID 20367186, compound

HRID 617020Notes

Reaction equation

HRID 617020 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([NH2:10])OCC)C.[CH3:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][NH:18][NH2:19])=[CH:15][CH:14]=1.N1C=CC=CC=1>C(O)C.O>[NH2:10][C:6]1[NH:19][N:18]([CH2:17][C:16]2[CH:20]=[CH:21][C:13]([CH3:12])=[CH:14][CH:15]=2)[C:4](=[O:3])[CH:5]=1

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 33348[(4-Methylphenyl)methyl]hydrazineHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl ester

Product 1

HCID 20367186HCID 20367186, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

17.5 g of β-amino-β-ethoxyacrylic acid ethyl ester and 13.6 g of 4-methylbenzylhydrazine are introduced into 75 ml of pyridine. The mixture is stirred for 8 hours at room temperature and the pyridine is driven off under reduced pressure. The residue is treated with a solution of 4.6 g of Na in 100 ml of ethanol and the mixture is warmed to 60° for 1 hour. The alcohol is driven off and the residue is taken up in 100 ml of water. The aqueous phase is extracted with ether, clarified with charcoal and acidified. A yellow-colored precipitate is obtained, which melts at 149° after recrystallisation from alcohol. The yield is 7.3 g of the compound identified above, corresponding to 36% of theory.

Workup

  1. temperaturethe mixture is warmed to 60° for 1 hour
  2. extractionThe aqueous phase is extracted with ether
  3. customA yellow-colored precipitate is obtained
  4. customwhich melts at 149° after recrystallisation from alcohol

Sources & evidence

ORD record
ord-e4142bf5f920413b9c2df06146dad62b
Source dataset
uspto-grants-1978_02
Patent number
US04076943

Reaction notes

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