Hydrochloric Acid → 4-Bromo-6-methoxyquinoline-3-carboxylic acid

HRID 639001Notes

Reaction equation

HRID 639001 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Br:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)=[O:5])C.[OH-].[Na+].CO.C(Cl)Cl.Cl>C1COCC1>[Br:16][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 49758155Ethyl 4-bromo-6-methoxyquinoline-3-carboxylate

Product 1

HCID 684531854-Bromo-6-methoxyquinoline-3-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-6-methoxy-quinoline-3-carboxylic acid ethyl ester (41 g, 0.132 mole), partially dissolved in THF (600 mL), was treated dropwise with aqueous 2 M sodium hydroxide (198.4 mL, 0.396 mole). After 24 hr, the reaction was complete by TLC (2% MeOH/CH2Cl2). The mixture was neutralized with 5 M HCl then the THF was removed in vacuo. The residue was dissolved in water and acidified with 5 M HCl. The solid product was collected under suction, washed well with water, and dried in vacuo to give the title compound (34 g, 91%) as a white solid: MS (ES) m/e 282/284 (M+H)+.

Workup

  1. customthe THF was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customThe solid product was collected under suction
  4. washwashed well with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-81f9e65b74694778aa3dc6b497c25f11
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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