Sulfuric Acid → HCID 69977541, compound

HRID 1282404Notes

Reaction equation

HRID 1282404 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:14]=[C:13]([Cl: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]([OH:30])(=[O:29])[CH:27]=[CH2:28]>O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[Cl:15][C:13]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH:28]=[CH:27][C:26]([OH:30])=[O:29])[CH:14]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 5987Sulfamic AcidHCID 6581Acrylic AcidHCID 666462-Amino-4-chlorobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 69977541HCID 69977541, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 5486778Palladium acetylacetonateCatalystHCID 962WaterSolvent2×

Procedure

At 2° C., a solution of 2.98 g of sodium nitrite in 5.65 ml of water is added to a mixture of 6.43 g of 2-amino-4-chlorobenzoic acid, 29.5 ml of water and 14.3 ml of concentrated sulfuric acid. 0.4 g of amidosulfonic acid are subsequently added, and this reaction mixture is then added dropwise to 2.7 g of acrylic acid and 28.5 mg of palladium acetylacetonate. After 4 hours at 40° C., the precipitated solid is filtered off, giving 7.48 g of 4-chloro-2-(3-hydroxy-3-oxo-1-propenyl)-benzoic acid of melting point 200-202° C.

Workup

  1. filtrationthe precipitated solid is filtered off

Sources & evidence

ORD record
ord-1079b489298d44cca85fe373357e8da2
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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