Sodium Hydroxide → 2-(Acetyl-allyl-amino)-6-chloro-isonicotinic acid

HRID 1664219Notes

Reaction equation

HRID 1664219 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([N:12]([C:16](=[O:18])[CH3:17])[CH2:13][CH:14]=[CH2:15])[CH:6]=1)C.[OH-].[Na+]>CO>[C:16]([N:12]([CH2:13][CH:14]=[CH2:15])[C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([Cl:11])[N:8]=1)[C:4]([OH:19])=[O:3])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866204832-(Acetyl-allyl-amino)-6-chloroisonicotinic acid ethyl ester

Product 1

HCID 866204802-(Acetyl-allyl-amino)-6-chloro-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1.08 g 2-(acetyl-allyl-amino)-6-chloro-isonicotinic acid ethyl ester (3.82 mmol) in 15 ml MeOH is treated with 5.5 ml 1N NaOH (5.5 mmol) and stirred at 25° C. for 30 min. The reaction is quenched with 6 ml 1 N HCl and with EtOAc extracted. Crystallization from a small amount of EtOAc gives the title compound as yellow crystals.

Workup

  1. customThe reaction is quenched with 6 ml 1 N HCl and with EtOAc
  2. extractionextracted
  3. customCrystallization from a small amount of EtOAc

Sources & evidence

ORD record
ord-bd171766e5c24c22ba2b44e2d5d30cb3
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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