Diethyl {[(pyridin-3-yl)amino]methylidene}propanedioate → Ethyl 4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate

HRID 1968702Notes

Reaction equation

HRID 1968702 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][CH:8]=[C:9]([C:15]([O:17]CC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[O:17]=[C:15]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][N:1]=2)[NH:7][CH:8]=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 1

HCID 2313092Diethyl {[(pyridin-3-yl)amino]methylidene}propanedioate

Product 1

HCID 2763116Ethyl 4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent2×

Procedure

To a solution of diphenyl ether (30 mL) at 250° C. was added a 1 mL diphenylether solution of diethyl [(pyridin-3-ylamino)methylidene]propanedioate (0.80 g, 3.0 mmol) dropwise over 5 minutes. After 30 minutes, the mixture was cooled to ambient temperature, diluted with hexanes (100 mL) and filtered. The solid was dried in vacuo, providing the titled compound.

Workup

  1. filtrationfiltered
  2. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-d9e4b25d173c44e0a6bf712fc41f7859
Source dataset
uspto-grants-2013_04
Patent number
US08426438B2

Reaction notes

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