Lithium hydroxide, monohydrate → 3-Bromo-5-[(dipropylamino)carbonyl]Benzoic Acid

HRID 13993

Reaction equation

HRID 13993 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>C1COCC1.O.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

Product 1

HCID 112903703-Bromo-5-[(dipropylamino)carbonyl]Benzoic Acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, PREPARATION 3, 1.4 g, 4.1 mmol) in THF/water/methanol (4/2/2, 8 mL) is added to lithium hydroxide monohydrate (0.17 g, 4.05 mmol). The mixture is stirred at 20 degrees-25 degrees C. for 1 hour and then solvent is removed under reduced pressure. The residue is dissolved in water (50 mL) and hydrochloric acid (1 N) is added to adjust the pH to about 3. The aqueous mixture is extracted with ethyl acetate and the organic phase is separated and dried over magnesium sulfate to give the title compound. Analytical calculated for C14H18BrNO3: C, 51.23; H, 5.53; N, 4.27; Br, 24.35. Found: C, 51.37; H, 5.56; N, 4.28.

Workup

  1. customsolvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in water (50 mL)
  3. additionhydrochloric acid (1 N) is added
  4. extractionThe aqueous mixture is extracted with ethyl acetate
  5. customthe organic phase is separated
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-2bd395877e524deeb1857eb1e0a7d7d2
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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