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

HRID 732456Notes

Reaction equation

HRID 732456 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:22])[C:7]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[N:10]=[C:9]([NH:17][C@H:18]([CH2:20][CH3:21])[CH3:19])[CH:8]=1)C.Cl>C(O)C>[C@@H:18]([NH:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[N:10]=1)[C:6]([OH:22])=[O:5])([CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68814656(S)-2-sec-Butylamino-6-difluoromethoxy-isonicotinic acid ethyl ester

Product 1

HCID 68815507(S)-2-sec-Butylamino-6-difluoromethoxy-isonicotinic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 2 N NaOH (0.67 mL) to (S)-2-sec-butylamino-6-difluoromethoxy-isonicotinic acid ethyl ester in ethanol (5 mL). Stir 3 h and acidify to about pH=4 with 1 N HCl and extract with ethyl acetate. Wash organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (0.1 g, 85%).

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialWash organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-54a4f06812ab46a59319e68fac5aff4c
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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