Citric Acid → 1379375-22-0

HRID 1426287Notes

Reaction equation

HRID 1426287 reaction equation
[F:1][CH:2]([F:14])[C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[F:14][CH:2]([F:1])[C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 696732014-Pyridinecarboxylic acid, 2-(difluoromethyl)-3-fluoro-, methyl ester

Product 1

HCID 696736881379375-22-0

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(difluoromethyl)-3-fluoroisonicotinate (0.44 g, 2.1 mmol, from Step 4) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.45 g, 11 mmol) in water (10 mL). The reaction was stirred for 2 hours. The reaction mixture was acidified by the addition of a solution of citric acid. The product was extracted with three portions of DCM. The combined extracts were dried over sodium sulfate, decanted and concentrated to afford product, which was used without further purification in Step 6. H NMR (300 MHz, CD3OD): δ 8.57 (d, 1H), 7.99 (dd, 1H), 6.96 (t, 1H).

Workup

  1. extractionThe product was extracted with three portions of DCM
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. customto afford product, which
  6. customwas used without further purification in Step 6

Sources & evidence

ORD record
ord-7a501e3dcb0c45dc98022dcd473e5a34
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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