Glycerol → 8-Bromo-6-quinolinecarboxylic acid
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Br:11].O[CH2:13][CH:14]([CH2:16]O)O.S(=O)(=O)(O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O>>[Br:11][C:3]1[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:9]=[C:10]2[C:2]=1[N:1]=[CH:16][CH:14]=[CH:13]2Participants
Conditions
- Temperature
- 50 °C
Procedure
4-Amino-3-bromo-benzoic acid (1 eq) and glycerol (2.4 eq) was added to sulfuric acid (6.4M, reaction conc. 0.6M) at 0° C. After 15 min, the bath was removed and 3-nitro-phenylsulfonic acid sodium salt (1.3 eq) was added portionwise. The reaction mixture was heated gradually until exothermic reaction started (between 110-140° C.), the internal temperature was maintained below 170° C. for 1 h. The reaction mixture was cooled to 50° C. and poured slowly into NH4OH-ice (2:1). The title product isolated by filtration, dissolved in warm 5% NH4OH/MeOH and diluted with CH2Cl2. This solution was filtered through silica gel eluting with (NH4OH, MeOH, CH2Cl2, 3:30:70). The residue was stirred in EtOH and the title product isolated by filtration.
Workup
- customthe bath was removed
- temperatureThe reaction mixture was heated gradually until exothermic reaction
- custom(between 110-140° C.)
- temperaturethe internal temperature was maintained below 170° C. for 1 h
Sources & evidence
- ORD record
- ord-4e9d1b4b731946d1bc42e47d3f728348
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482456B2
Reaction notes
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