Hydrochloric Acid → HCID 58934756, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[NH:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19]CC)=[O:18])=[CH:5]2.[OH-].[Li+].Cl.C(OCC)C>CO.O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[NH:8][CH:7]([C:13]([F:15])([F:16])[F:14])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2Participants
Procedure
Ethyl 6,8-dibromo-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate (732.0 mg, 1.70 mmol) was suspended in methanol-tetrahydrofuran-water (5 mL, 7:2:1). Lithium hydroxide (214 mg, 5.108 mmol) was added and the mixture was gently heated to reflux for two hours. The reaction was cooled to room temperature and 1 N aqueous hydrochloric acid added until pH=1. The organic solvent was removed in vauco to afford a suspension of a crude yellow solid. Diethyl ether (50 mL) was added, and the solution was washed with water (2×50 mL), saturated ammonium chloride (2×50 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield 6,8-dibromo-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid (633.0 mg, 1.52 mmol) as a yellow solid (89% yield): 1H NMR (CD3OD3, 300 MHz)7.07 (s, 1H), 7.57 (d, 1H, J=2.0 Hz), 7.39 (d, 1H, J=2.0 Hz), 5.26 (m, 1H). Anal. Calcd for C11H6Br2F3NO3: C, 32.95; H, 1.51; N, 3.49. Found: C, 32.88; H, 1.51; N, 3.46.
Workup
- temperaturethe mixture was gently heated
- temperatureto reflux for two hours
- customThe organic solvent was removed in vauco
- customto afford
- additiona suspension of a crude yellow solid
- washthe solution was washed with water (2×50 mL), saturated ammonium chloride (2×50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-a777228d9d0d4c6c94ec28be08d46860
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259266B2
Reaction notes
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