HCID 68826262, compound → HCID 58585806, compound

HRID 1297669Notes

Reaction equation

HRID 1297669 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]=[C:13]([C:19]#[N:20])[C:14]([O:16]CC)=O)=[CH:7][CH:6]=1)[CH3:2]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[NH:11][CH:12]=[C:13]([C:19]#[N:20])[C:14]2=[O:16])=[O:21])[CH3:2]

Participants

3

Reactant 1

HCID 68826262HCID 68826262, compound

Product 1

HCID 58585806HCID 58585806, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

The mixture of 4-(2-cyano-2-ethoxycarbonyl-vinylamino)-benzoic acid ethyl ester (55 g, 0.19 mol) in diphenyl ether (300 mL) was stirred under reflux for 4 h. HPLC showed all the starting material disappeared. After cooling to 40° C., the solution was poured into petroleum ether (1000 mL). The solid was filtered, washed with petroleum ether, ethyl acetate and dried to give 3-cyano-4-oxo-1,4-dihydro-quinoline-6-carboxylic acid ethyl ester as a brown solid (39 g, 85%). HPLC showed 90% purity. LC-MS m/e 243 (MH+)

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationThe solid was filtered
  3. washwashed with petroleum ether, ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-ea86d79b527f4a6da9dd42427c127748
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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