Acetic Acid → HCID 178488028, compound

HRID 973576Notes

Reaction equation

HRID 973576 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=O)[C:6]([NH2:12])=[CH:5][CH:4]=1.C(O)(=O)C.[O-:17][C:18]#[N:19].[K+].[OH-].[Na+]>O>[OH:17][C:18]1[N:19]=[C:8]([OH:10])[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[N:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2779305-Methoxyanthranilic acidHCID 11378442Potassium cyanate

Product 1

HCID 178488028HCID 178488028, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 5-methoxy anthranilic acid (40 g, 0.24M), acetic acid (18.0 g, 0.3M) and 1 liter warm water (35° ) was stirred and allowed to cool. A solution of potassium cyanate (24.3 g, 0.3M) in water (100 ml) was added over 15 minutes and then stirred for a further 30 minutes. Sodium hydroxide (320 g, 8.0M) solid was added portionwise and the reaction was then heated at 90° for 30 minutes and allowed to cool overnight. The solid was filtered off and dissolved in hot water (500 ml) and then acidified with dilute sulphuric acid to precipitate the product. The solid was filtered off and washed free of acid with water and then dried at 100°/vacuum to yield the title compound (37.7 g) m.p. >290°.

Workup

  1. temperatureto cool
  2. stirringstirred for a further 30 minutes
  3. temperaturethe reaction was then heated at 90° for 30 minutes
  4. temperatureto cool overnight
  5. filtrationThe solid was filtered off
  6. dissolutiondissolved in hot water (500 ml)
  7. customto precipitate the product
  8. filtrationThe solid was filtered off
  9. washwashed free of acid with water
  10. customdried at 100°/vacuum

Sources & evidence

ORD record
ord-640869982d444131b334acc274174d05
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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