1,3-Diethyl 2-oxopropanedioate → HCID 68473442, compound

HRID 240368Notes

Reaction equation

HRID 240368 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][CH:3]=1.O=[C:17]([C:23](OCC)=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19].FC1C=C(N2C(=O)C(C(O)=O)=NC3C=CC=NC2=3)C=CC=1C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:15]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]2=[O:24])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 675311174-(3-Fluoro-4-methylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxylic acidHCID 67531613HCID 67531613, compound

Product 1

HCID 68473442HCID 68473442, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

19.8 g (0.1 mol) of N-(6-methylpyridine-2-yl)benzene-1,2-diamine was dissolved in toluene (100 ml), and 19.0 g (0.11 mol) of diethyl ketomalonate and 57.1 g of 4 A molecular sieve were added thereto. The solution was heated to reflux for 3 hours while removing water using a Dean-Stark apparatus. Reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 27.2 g (yield: 89%) of ethyl 1-(6-methylpyridine-2-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 hours
  3. customwhile removing water using a Dean-Stark apparatus
  4. customReaction mixture
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9edad7f4efeb49a8b6f6cf659d1a22b9
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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