Acetic Acid → 2-(4-Amino-2-ethoxyphenyl)-1H-isoindole-1,3(2H)-dione

HRID 2290549Notes

Reaction equation

HRID 2290549 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23])[CH3:2].C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.[Fe]>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23])[NH2:10])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 202314402-(2-Ethoxy-4-nitrophenyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 202314372-(4-Amino-2-ethoxyphenyl)-1H-isoindole-1,3(2H)-dioneYield 36.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 9.2 g (0.03 mole) of 2-(2-ethoxy-4-nitrophenyl)-1H-isoindol-1,3(2H)-dione and 12.8 g (0.23 mole) of iron powder in 50 ml of water was heated at 100° C. During a two hour period 35.1 g (0.58 mole) of glacial acetic acid was added to the hot reaction mixture. After complete addition the mixture was heated at reflux for four hours. The reaction mixture was cooled then made basic by the addition of potassium carbonate. The basic mixture was extracted with 500 ml of methylene chloride. The extract was filtered, and the filtrate extracted with 300 ml of 2N hydrochloric acid. The acidic extract was made basic with cold concentrated ammonium hydroxide. The basic solution was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under the reduced pressure to produce 3.1 g of 3-ethoxy-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)aniline as a solid.

Workup

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureat reflux for four hours
  4. temperatureThe reaction mixture was cooled
  5. extractionThe basic mixture was extracted with 500 ml of methylene chloride
  6. filtrationThe extract was filtered
  7. extractionthe filtrate extracted with 300 ml of 2N hydrochloric acid
  8. extractionThe acidic extract
  9. extractionThe basic solution was extracted with methylene chloride
  10. dry with materialThe extract was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customthe filtrate evaporated under the reduced pressure

Sources & evidence

ORD record
ord-d687e26a7f07479ea5b0988497e7a1fe
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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