Sodium Hydroxide → HCID 59834439, compound

HRID 2199117Notes

Reaction equation

HRID 2199117 reaction equation
C[O:2][C:3](=[O:26])[C:4]([NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[N:16]=[N:17][C:18]([Cl:24])=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:20]=2)=[C:9]([Cl:25])[CH:8]=1)=[O:5].[OH-].[Na+]>CO>[Cl:13][C:11]1[CH:12]=[C:7]([NH:6][C:4](=[O:5])[C:3]([OH:26])=[O:2])[CH:8]=[C:9]([Cl:25])[C:10]=1[O:14][C:15]1[N:16]=[N:17][C:18]([Cl:24])=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59834491HCID 59834491, compound

Product 1

HCID 59834439HCID 59834439, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid methyl ester (27) (1.87 g, 4.47 mmol) in methanol (35 mL) at 0° C. was treated with a 1N aqueous sodium hydroxide solution (8.95 mL, 8.95 mmol). The reaction mixture was warmed to room temperature and stirred for 2 h. The solvent was concentrated under vacuum. The residue was diluted with water (500 mL), and the mixture was made acidic to pH=1-2 by the addition of a 1N aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate (2×250 mL). The organic layer was separated, dried with magnesium sulfate, filtered and concentrated. The resulting solid was dried on high vacuum overnight to afford N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid (28) (1.77 g, 98%) as a white solid; EI(+)-HRMS m/z calcd for C15H12Cl3N3O4 (M+H) 403.9966, found 403.9968. Molecular Weight=404.6396; Exact Mass=402.9893

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. additionThe residue was diluted with water (500 mL)
  3. additionthe mixture was made acidic to pH=1-2 by the addition of a 1N aqueous hydrochloric acid solution
  4. extractionThe mixture was extracted with ethyl acetate (2×250 mL)
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting solid was dried on high vacuum overnight

Sources & evidence

ORD record
ord-8d8a5ec94767446884ed182d9f51c834
Source dataset
uspto-grants-2016_06
Patent number
USRE046024E1

Reaction notes

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