Ammonia → 5-Aminophthalide

HRID 978648Notes

Reaction equation

HRID 978648 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])N[C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[OH-].[Na+].N>O.[Zn]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:7])[O:10][CH2:9]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 729154-Aminophthalimide

Product 1

HCID 7206695-Aminophthalide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Twenty grams of 4-aminophthalimide was added to a mixture of 41 gm zinc and 122 gm sodium hydroxide in 50 ml water (with good stirring) over 30 minutes. The mixture was stirred another 30 minutes, then heated to 60°. When ammonia ceased to be evolved the mixture was heated for an additional 60 minutes, then cooled to about 30°. The zinc residues were filtered off and the solution was acidified with 30 ml concentrated hydrochloric acid. The solution was heated to 90° for 45 minutes, then cooled and neutralized with 20 gm solid sodium carbonate, which brought the pH to 8-9. The product was filtered, washed with water and air dried. Wt=16.8 gm, m.p.=177°-189°.

Workup

  1. temperatureheated to 60°
  2. temperaturewas heated for an additional 60 minutes
  3. temperaturecooled to about 30°
  4. filtrationThe zinc residues were filtered off
  5. temperatureThe solution was heated to 90° for 45 minutes
  6. temperaturecooled
  7. filtrationThe product was filtered
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-0559cc93cf5f425f98d2c7782dfb7bf0
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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