Nitrogen → HCID 14075281, compound

HRID 986572Notes

Reaction equation

HRID 986572 reaction equation
[CH2:1]([NH:3][C:4]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[C:18](OCC)(=[O:23])[CH2:19][C:20]([CH3:22])=O.N#N>>[CH2:1]([N:3]1[C:20]([CH3:22])=[CH:19][C:18](=[O:23])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]1[C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[CH3:2]

Participants

4

Reactant 3

HCID 947NitrogenHCID 8868Ethyl AcetoacetateHCID 70373462HCID 70373462, compound

Product 1

HCID 14075281HCID 14075281, compoundYield 33.3%

Conditions

Temperature
170 °C

Procedure

6 g of ethyl beta-ethylamino-4-chlorocinnamate and 12 g of ethyl acetoacetate is mixed in a 50 ml 3-neck flask fitted with a N2 -inlet, magnetic stirring bar, thermometer and a short-path distillation head (with receiver). The reaction mixture is heated (170° C.) for 10 hours. Ethanol and water is collected in the distillation receiver. The reaction mixture are cooled and triturated with ethyl acetate/ether to yield 2.52 g of ethyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate.

Workup

  1. distillationEthanol and water is collected in the distillation receiver
  2. temperatureThe reaction mixture are cooled
  3. customtriturated with ethyl acetate/ether

Sources & evidence

ORD record
ord-afe3b795080448e0b580a3eb2f5826b9
Source dataset
uspto-grants-1987_12
Patent number
US04714492

Reaction notes

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