Hydrochloric Acid → (S)-2-sec-Butylamino-6-cyano-isonicotinic acid

HRID 732413Notes

Reaction equation

HRID 732413 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[N:7]=[C:6]([NH:12][C@H:13]([CH2:15][CH3:16])[CH3:14])[CH:5]=1.[OH-].[Na+].Cl>CO>[C@@H:13]([NH:12][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]#[N:11])[N:7]=1)[C:3]([OH:17])=[O:2])([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68814564(S)-2-sec-Butylamino-6-cyano-isonicotinic acid methyl ester

Product 1

HCID 68814560(S)-2-sec-Butylamino-6-cyano-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve (S)-2-sec-butylamino-6-cyano-isonicotinic acid methyl ester (250 mg, 0.93 mmol) in methanol (3 mL). Slowly add 2 N NaOH (1.5 mL) and stir overnight at room temperature. Acidify to about pH=6 with 5 N HCl and concentrate. Dilute with ethyl acetate (20 mL) and wash the organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. concentrationconcentrate
  2. additionDilute with ethyl acetate (20 mL)
  3. washwash the organic layer with saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9d18502c30cb44ef82df76a491976745
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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