Sulfuric Acid → HCID 69978127, compound

HRID 1282401Notes

Reaction equation

HRID 1282401 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.NS(O)(=O)=O.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>O.C(O)(C)C.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[F:15][C:13]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH:28]=[CH:27][C:26]([O:30][CH3:31])=[O:29])[CH:14]=1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 5987Sulfamic AcidHCID 7294Methyl AcrylateHCID 27249674-Fluoroanthranilic acidHCID 23668193Sodium Nitrite

Product 1

HCID 69978127HCID 69978127, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 5486778Palladium acetylacetonateCatalystHCID 962WaterSolvent3×HCID 3776IsopropanolSolvent

Procedure

At 0C, a solution of 0.52 g of sodium nitrite in 1 ml of water is added within a period of 30 minutes to a mixture of 1 g of 2-amino-4-fluorobenzoic acid, 15 ml of water and 6.24 ml of concentrated sulfuric acid. The mixture is then stirred for one hour. Following addition of 0.3 g of amidosulfonic acid, 0.7 g of methyl acrylate in 9 ml of isopropanol are added dropwise, and 10 mg of palladium acetylacetonate are added. After 4 hours at 40° C., 30 ml of water are added and the resulting precipitate is filtered off. Drying gives 1.1 g of 4-fluoro-2-(3-methoxy-3-oxo-1-propenyl)-benzoic acid of melting point 151-153° C.

Workup

  1. additionare added dropwise
  2. waitAfter 4 hours at 40° C.
  3. filtrationthe resulting precipitate is filtered off
  4. customDrying

Sources & evidence

ORD record
ord-87856a5e97a944ef949ffef218558d37
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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