Acetic Acid → HCID 86150265, compound

HRID 1590284Notes

Reaction equation

HRID 1590284 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.CCOCC>[Cl:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:14]([C:15](=[O:16])[CH3:17])[C:13]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 126677132-Chloro-3-nitrobenzaldehyde

Product 1

HCID 86150265HCID 86150265, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-chloro-3-nitrobenzaldehyde (2.00 g., 10.8 mmole), ethyl acetoacetate (1.37 ml., 10.78 mmole), piperidine (0.25 ml.) and acetic acid (0.5 ml.) in benzene (21 ml.) under argon is fitted with a Dean-Stark trap and heated at 110° (oil bath) for 3 hours. The reaction is diluted with ether and washed with saturated sodium bicarbonate, 1N hydrochloric acid, and saturated sodium chloride, dried over anhydrous magnesium sulfate, and evaporated to give 2-[(2-chloro-3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester as a red oil (3.42 g.). TLC (silica gel; ether/hexanes) Rf =0.31 and 0.43.

Workup

  1. temperatureheated at 110° (oil bath) for 3 hours
  2. washwashed with saturated sodium bicarbonate, 1N hydrochloric acid, and saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-33fd9d945b984c1b9346f6c6b38f23bf
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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