Lithium hydroxide, monohydrate → 3-[(Dimethylamino)methyl]-5-fluorobenzoic acid

HRID 1426293Notes

Reaction equation

HRID 1426293 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([F:15])[CH:14]=1)[C:8]([O:10]C)=[O:9])[CH3:3].O.[OH-].[Li+]>O1CCCC1.O>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([F:15])[CH:14]=1)[C:8]([OH:10])=[O:9])[CH3:1]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69672877Methyl 3-[(dimethylamino)methyl]-5-fluorobenzoate

Product 1

HCID 696731623-[(Dimethylamino)methyl]-5-fluorobenzoic acidYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[(dimethylamino)methyl]-5-fluorobenzoate (0.040 g, 0.19 mmol from Step 3) was dissolved in tetrahydrofuran (3 mL) and lithium hydroxide monohydrate (0.0954 g, 2.27 mmol) dissolved in water (1 mL) was added. The reaction was stirred for 3 hours. The crude reaction mixture was purified by preparative HPLC-MS (C18, eluting with a gradient of H2O/MeCN containing 0.15% NH4OH). The eluent containing the desired mass was evaporated using rotary evaporation to afford product (22 mg, 59%), which was used directly in Step 5. LCMS (M+H)+: 198.1.

Workup

  1. additionwas added
  2. customThe crude reaction mixture
  3. customwas purified by preparative HPLC-MS (C18
  4. washeluting with a gradient of H2O/MeCN containing 0.15% NH4OH)
  5. additionThe eluent containing the desired mass
  6. customwas evaporated
  7. customevaporation

Sources & evidence

ORD record
ord-43a2ea5f4f8e4145802181c1e433c6c2
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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