Lithium Hydroxide → HCID 70896138, compound

HRID 2403694Notes

Reaction equation

HRID 2403694 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([O:14]CC)=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:17][CH3:18].[OH-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70896141HCID 70896141, compound

Product 1

HCID 70896138HCID 70896138, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-bromo-6-methoxyquinoline-3-carboxylate (250 mg, 0.80 mmol) in tetrahydrofuran (5 mL) was added 1 N aqueous lithium hydroxide (1.6 mL, 1.6 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and the residue was taken up in water and 1 N aqueous lithium hydroxide (0.4 mL). The solution was extracted twice with ethyl acetate. The aqueous layer was then acidified to pH=4 with 1 N aqueous hydrochloric acid. The resulting precipitate was filtered, washed with water, and dried under vacuum to give the title compound (165 mg, 73%) as an off-white solid. +ESI (M+H+1) 284.1; 1H NMR (400 MHz, CD3OD, δ): 9.19 (d, J=2.15 Hz, 1 H), 8.89 (d, J=1.76 Hz, 1 H), 8.30 (s, 1 H), 7.53 (s, 1 H), 4.04 (s, 3 H).

Workup

  1. concentrationThe reaction was concentrated
  2. extractionThe solution was extracted twice with ethyl acetate
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-97154060bb204fd0896069f3aa618260
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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