Hydrochloric Acid → HCID 21883649, compound

HRID 854943Notes

Reaction equation

HRID 854943 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:21])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.[OH-].[Li+].Cl.C(OCC)C>CO.O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:21])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]([C:12]([F:14])([F:15])[F:13])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 69516171HCID 69516171, compound

Product 1

HCID 21883649HCID 21883649, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl 8-bromo-6-methyl-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylate (1.8 g , 4.95 mmol) was suspended in methanol-tetrahydrofuran-water (20 mL, 7:2:1). Lithium hydroxide (414 mg, 9.88 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 sulfate (2×50 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to yield 8-bromo-6-methyl-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid (1.3 g, 4.05 mmol) as a yellow solid (82% yield). 1H NMR (300 MHz, CDCL3) 7.78 (s, 1H), 7.82 (s, 1H), 6.59 (s, 1H), 5.20 (m, 2H), 5.13 (bs, 1H), 2.34 (s, 1H). HRMS m/z 334.9763; (M+, C12H9BrF3NO2 calcd 334.9769).

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 (2×50 mL), saturated ammonium sulfate (2×50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-93cec7e89ac04be8a48a2985b84ee15c
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…