Sodium Hydroxide → HCID 90409699, compound

HRID 516599Notes

Reaction equation

HRID 516599 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[C:11]([F:19])[CH:10]=2)[N:5]=[C:4]([C:20]([O:22]C)=[O:21])[C:3]=1[Cl:24].[OH-].[Na+]>CO>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[C:11]([F:19])[CH:10]=2)[N:5]=[C:4]([C:20]([OH:22])=[O:21])[C:3]=1[Cl:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90409305HCID 90409305, compound

Product 1

HCID 90409699HCID 90409699, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask charged with MeOH (2 mL) was added methyl 4-amino-3-chloro-6-(4-(difluoromethoxy)-3-fluorophenyl)-5-fluoropicolinate (190 mg, 0.52 mmol) and sodium hydroxide 2 M solution (1 mL, 1 mmol). Following 12 h of mechanical stirring, the reaction mixture was concentrated using a rotary evaporator with a water bath temperature of 40° C. Water was added to the resulting oil and the solution was slowly acidified by the addition of concentrated HCl until a tan precipitate formed. Filtration using filter paper and a Büchner funnel afforded the title compound as a tan solid (108 mg).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customa rotary evaporator with a water bath temperature of 40° C
  3. additionWater was added to the resulting oil
  4. additionthe solution was slowly acidified by the addition of concentrated HCl until a tan precipitate
  5. customformed
  6. filtrationFiltration
  7. filtrationusing filter paper

Sources & evidence

ORD record
ord-aa60ed451a3e467a8ddeac51c456c00f
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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