Sodium Hydroxide → 6-(N-Boc-N-2-picolylaminomethyl)nicotinic Acid

HRID 11846

Reaction equation

HRID 11846 reaction equation
[C:1]([N:8]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][N:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([N:8]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21973709Methyl 6-(N-Boc-N-2-picolylaminomethyl)nicotinate

Product 1

HCID 219736636-(N-Boc-N-2-picolylaminomethyl)nicotinic AcidYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 12-2 (351.3 mg) was dissolved in methanol (3.5 ml) and THF (3.5 ml). After the addition of 1 mol/l aqueous solution of sodium hydroxide (3.5 ml), the mixture was stirred for 2 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in distilled water (1.2 ml) and aqueous solution of hydrochloric acid (1 mol/l) was added to adjust the pH to 4. The mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain the target compound (277.9 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in distilled water (1.2 ml)
  4. additionaqueous solution of hydrochloric acid (1 mol/l) was added
  5. extractionThe mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-a78d72c6fe744272bcfd3a458c7ab371
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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