Anthranilic Acid → HCID 223057, compound

HRID 484559Notes

Reaction equation

HRID 484559 reaction equation
N([O-])=O.[Na+].[C:5]([OH:14])(=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)N.OS(O)(=O)=O.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:7]1([CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]([C:5]([OH:14])=[O:13])=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 1118Sulfuric AcidHCID 7501StyreneHCID 23668193Sodium Nitrite

Product 1

HCID 223057HCID 223057, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent3×

Procedure

20.7 g of sodium nitrite in 50 ml of water are added dropwise at 0°-5° C. to 41.1 g of anthranilic acid and 24 ml of conc. H2SO4 in 300 ml of water and the mixture is stirred at this temperature for 20 minutes. An excess of nitrite which may be present is destroyed by addition of sulphamic acid. The solution of the diazonium salt prepared in this way is added dropwise at about 60° C. to a rapidly stirred mixture of 62.4 g of styrene and 20 ml of water, and immediately after the start of addition the mixture is treated with 68 mg of Pd(OAc)2. After addition and evolution of gas are complete, the mixture is allowed to cool and the solid is filtered off with suction, washed with warm water and dried at 60° C. 62.5 g (93%) of stilbene-2-carboxylic acid of m.p. 158°-159° C. are obtained, Lit 158 -160° C., Chem. Ber. 27, 2506 (1894).

Workup

  1. customAn excess of nitrite which may be present is destroyed by addition of sulphamic acid
  2. customThe solution of the diazonium salt prepared in this way
  3. additionimmediately after the start of addition the mixture
  4. additionAfter addition and evolution of gas
  5. temperatureto cool
  6. filtrationthe solid is filtered off with suction
  7. washwashed with warm water
  8. customdried at 60° C

Sources & evidence

ORD record
ord-bc9bbfe654a94d5daf57c5b15566c09a
Source dataset
uspto-grants-1993_07
Patent number
US05231223

Reaction notes

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