Diethyl Ether → 6-Iodo-4-oxo-1,4-dihydroquinoline-3-carbonitrile

HRID 1297628Notes

Reaction equation

HRID 1297628 reaction equation
C(O[C:4](=[O:17])/[C:5](/[C:15]#[N:16])=[CH:6]\[NH:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1)C.C(OC(=O)/C(/C#N)=C/NC1C=CC(I)=CC=1)C.CCOCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[I:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]([C:15]#[N:16])[C:4]2=[O:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6013301709637-42-3HCID 6379342HCID 6379342, compound

Product 1

HCID 289765906-Iodo-4-oxo-1,4-dihydroquinoline-3-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
260 °C

Procedure

A mixture of (Z)-2-cyano-3-(4-iodo-phenylamino)-acrylic acid ethyl ester and (E)-2-cyano-3-(4-iodo-phenylamino)-acrylic acid ethyl ester (example 14a, 150 g, 0.44 mol) in diphenylether (1500 mL) was refluxed at 260° C. for 12 h. After cooling, ether was added. The solid was collected by filtration, washed with ether and dried to obtain 6-iodo-4-oxo-1,4-dihydro-quinoline-3-carbonitrile (110.5 g, 85%) as a black solid. LC-MS m/e 297 (MH+).

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was collected by filtration
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-a4002850a0bd410ba8f1525b31925111
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

Loading…