Ethyl 2-pyridylacetate → HCID 135626446, compound

HRID 2412422Notes

Reaction equation

HRID 2412422 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25](OCC)=[O:26].CC(C)([O-])C.[K+]>C(OCC)C>[OH:16][C:14]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:25](=[O:26])[C:24]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1

Participants

5

Reactant 3

HCID 75960Ethyl 2-pyridylacetateHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 135626446HCID 135626446, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

To a stirred solution of 5.8 gm of methyl 2-phenylamino-3-pyridine carboxylate and 25 gm of ethyl 2-pyridylacetate there is added, portionwise, 5.7 gm of potassium tertiary butoxide under a nitrogen atmosphere. The system is heated to an internal temperature of 105° C. for 10 minutes. The reaction is cooled to room temperature, diluted with 100 ml of diethyl ether and the brown precipitate collected by filtration. The precipitate is washed with 200 ml water and the filtrate is acidified to pH 3-4 with a 15% HCl solution whereupon the product separates. The precipitate is filtered and dried to give 6.3 gm of crude 4-hydroxy-1-phenyl-3-(2-pyridyl)-1,8-naphthyridin-2(1H)one; recrystallization from pyridine yields the title product; m.p. 332°-333° C.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationthe brown precipitate collected by filtration
  3. washThe precipitate is washed with 200 ml water
  4. filtrationThe precipitate is filtered
  5. customdried

Sources & evidence

ORD record
ord-5ea29eee47ea4f22a8d2913e663cb8d7
Source dataset
uspto-grants-1985_01
Patent number
US04492702

Reaction notes

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