Hydrochloric Acid → HCID 68576495, compound

HRID 638992Notes

Reaction equation

HRID 638992 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]CC)=[O:16].[OH-].[Na+].Cl>O1CCCC1.O>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68576825HCID 68576825, compound

Product 1

HCID 68576495HCID 68576495, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-bromo-8-fluoro-6-(methoxy)-3-quinolinecarboxylate (12.2 g, 37.3 mmol) in tetrahydrofuran (450 mL) was diluted by addition of a solution of sodium hydroxide 2N (27 mL) in water (75 mL). The reaction mixture was stirred overnight at room temperature then acidified to pH 3 with a solution of hydrogen chloride 5N. The solvents were evaporated to half the volume in vacuo. The reaction mixture was acidified to pH 1 by further addition of hydrogen chloride 5N, cooled to 4° C. for 30 minutes then filtered. The precipitate was dried in vacuo to afford the product as a white solid (10.1 g, 90%); MS (+ve ion electrospray) m/z 301 (MH+).

Workup

  1. customThe solvents were evaporated to half the volume in vacuo
  2. additionThe reaction mixture was acidified to pH 1 by further addition of hydrogen chloride 5N
  3. temperaturecooled to 4° C. for 30 minutes
  4. filtrationthen filtered
  5. customThe precipitate was dried in vacuo

Sources & evidence

ORD record
ord-33e384712008485d9df5dc22721f5460
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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