Acetic Acid → HCID 20159007, compound

HRID 985992Notes

Reaction equation

HRID 985992 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]3)[CH:3]=1.[Br:19]Br.C(O)(=O)C.C(N(CC)CC)C>CCOCC>[Br:19][C:12]1[C:13](=[O:18])[NH:14][C:15]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)=[CH:17][CH:16]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 24408BromineHCID 13728853HCID 13728853, compound

Product 1

HCID 20159007HCID 20159007, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6-(3-pyridyl)-2-(1H)-quinolone monohydrochloride (0.50 g), bromine (3.2 g), acetic acid (10 cm3) and triethylamine (0.195 g) was heated under reflux for 24 hours and then cooled. Ether (20 cm3) was then added to the cooled reaction mixture and the resulting yellow solid was filtered off. This material was purified by preparative layer chromatography eluting with chloroform:methanol, 15:1 (4 elutions), to afford 3-bromo-6-(3-pyridyl)-2-(1H)-quinolone, m.p. 297°-300°, (0.11 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. filtrationthe resulting yellow solid was filtered off
  5. customThis material was purified by preparative layer chromatography
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-b722d3b65a664817988ec584edce4ce2
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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