Methane → 5-Bromoimidazo-[1,2-a]-quinoline-2-carboxylic acid

HRID 1277970Notes

Reaction equation

HRID 1277970 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH:12]=[C:13]([C:15]([O:17]CC)=[O:16])[N:14]=[C:4]2[CH:3]=1.[OH-].[Na+].Cl.C>O.C(O)C.C(Cl)(Cl)Cl.CO>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[N:14]=[C:4]2[CH:3]=1

Participants

9

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12763980Ethyl 5-bromoimidazo-[1,2-a]-quinoline-2-carboxylate

Product 1

HCID 127639795-Bromoimidazo-[1,2-a]-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

1.28 g of ethyl 5-bromoimidazo-[1,2-a]-quinoline-2-carboxylate were heated on a steam bath with 5 ml of 1 N sodium hydroxide solution in 20 ml of water and 50 ml of ethanol until a clear solution was obtained (approx. 15 mins). 5 ml of 1 N hydrochloric acid were then added thereto and the solution was allowed to cool slowly to room temperature. The pale green crystals thus formed were filtered off and were washed with methanol. The mother liquors were reduced in volume and cooled to give a second crop. The two crops were combined in 50 ml of chloroform and 50 methanol and the solution obtained was decolorized with charcoal. The solution was reduced in volume under vacuum and the residue was cooled in ice to give colorless plates of 5-bromoimidazo-[1,2-a]-quinoline-2-carboxylic acid melting at 288°-90° C. (decomp).

Workup

  1. customwas obtained (approx. 15 mins)
  2. customThe pale green crystals thus formed
  3. filtrationwere filtered off
  4. washwere washed with methanol
  5. temperaturecooled
  6. customto give a second crop
  7. temperaturethe residue was cooled in ice

Sources & evidence

ORD record
ord-1264cf640d914490ad1cae440b157eb7
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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