Hydrochloric Acid → HCID 11380767, compound

HRID 854947Notes

Reaction equation

HRID 854947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]([C:13]([F:16])([F:14])[F:15])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 69516975HCID 69516975, compound

Product 1

HCID 11380767HCID 11380767, compoundYield 2,627.5%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl 6-chloro-8-methyl-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate (4.5, 0.51 mmol) was suspended in methanol-tetrahydrofuran-water (50 mL, 7:2:1). Lithium hydroxide (1.70 g, 42.3 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 (200 mL) was added, and the solution was washed with water (2×200 mL), saturated ammonium sulfate (2×200 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield 6-chloro-8-methyl-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid (3.8 g, 13.4 mmol) as a yellow solid (95% yield). (CDCl3, 300 MHz) 7.56 (s, 1H), 6.93 (s, 1H), 6.90 (s, 1H), 5.11 (q, 1H, J=7.2 Hz), 4.78 (bs, 1H), 2.08 (s, 3H). HRMS m/z 291.0286(M+, C12H9ClF3NO2, calcd 291.0274).

Workup

  1. temperaturethe mixture was gently heated
  2. temperatureto reflux for two hours
  3. customThe organic solvent was removed in vauco
  4. customto afford
  5. additiona suspension of a crude yellow solid
  6. washthe solution was washed with water (2×200 mL), saturated ammonium sulfate (2×200 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1bfc582a7fc14da59fcb91d53738df35
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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