8-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 8-Iodo-4(1H)-quinolinone

HRID 1864178Notes

Reaction equation

HRID 1864178 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8](C(O)=O)[C:7]2=[O:15]>C1(OC2C=CC=CC=2)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=[O:15]

Participants

3

Reactant 1

HCID 218975788-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 124036908-Iodo-4(1H)-quinolinoneYield 32.6%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

8-Iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (15.69 g, 49.8 mmol) was suspended in phenylether (40 mL) and the mixture heated to boiling. After 30 min, reaction was completed by LCMS. The crude was transferred to a bequer and cooled to room temperature. Hexanes (500 mL) were added and the mixture was stirred for 10 min. The solid was retrieved by filtration, thoroughly washed with hexanes and purified by HPLC to afford 8-iodo-1H-quinolin-4-one as a brownish solid (4.4 g, 23%). 1H NMR (DMSO-d6, 400MHz) δ 6.14 (d, 1H), 7.09 (t, 1H), 7.88 (d, 1H), 8.08 (dd, 1H), 8.16 (dd, 1H). Exact mass calculated for C9H6INO 270.95, found 271.8 (MH+).

Workup

  1. temperaturethe mixture heated to boiling
  2. customreaction
  3. filtrationThe solid was retrieved by filtration
  4. washthoroughly washed with hexanes
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-c716b0a1855e4ae78eee8897f5ce373b
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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