Acetic Acid → HCID 18411559, compound

HRID 992238Notes

Reaction equation

HRID 992238 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=3)[C:8](=[O:9])[C:7]2=[CH:22][CH:23]=1)([O-])=O.CC(O)=O>O1CCOCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][CH:18]=3)[C:8](=[O:9])[C:7]2=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 746816HCID 746816, compound

Product 1

HCID 18411559HCID 18411559, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-nitro-N-(p-carboxyphenyl)phthalimide (145) (0.2 g, 0.6 mmol) partially dissolved in 30 ml of 1,4-dioxane and 2 ml HOAc was added to a three necked round bottom flask equipped with a rubber septum, a gas inlet adapter and an adapter tightly fitted with a balloon. After the reaction vessel was purged three times with N2, 0.02 g of 10% Pd on activated charcoal was added. The reaction vessel was then flushed three times with H2. The heterogenous mixture was vigorously stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration through a celite pad and the filtrate concentrated under vacuum to give a bright yellow solid. The crude material which contained unreacted nitro compound was resubjected to the above procedure. Resulting crude material was triturated with hot 1,4-dioxane and undissolved material removed by filtration. The filtrate was diluted with water. The ensuing solid was filtered through a Buchner funnel and washed three times with 1 ml water. The product was dried in air for a short time and then in vacuo for 48-72 hours to afford 0.071 g (39%) 165 as a dark yellow solid: mp=270-271° C.; Rf0.88 (A): Rf0.80 (C): Rf0.49 (D): IR (cm−1): 3366 (NH), 3193 (NH), 2750-3200 (OH), 3075 (C═CH), 2669 (C—H), 1767 (C═O), 1752 (C═O), 1701 (bs, C═O), 1637 (C═C), 1607 (C═C), 1514 (C═C), 1482 (C═C), 1370 (C—N), 1220 (C—O), 740 (C═CH); MS m/z (rel intensity) 282 (16), 281 (100), 237 (71) 120 (43).

Workup

  1. customequipped with a rubber septum, a gas inlet adapter and an adapter
  2. customtightly fitted with a balloon
  3. customAfter the reaction vessel was purged three times with N2, 0.02 g of 10% Pd on activated charcoal
  4. additionwas added
  5. customThe reaction vessel was then flushed three times with H2
  6. customThe catalyst was removed by filtration through a celite pad
  7. concentrationthe filtrate concentrated under vacuum
  8. customto give a bright yellow solid
  9. customResulting crude material
  10. customwas triturated with hot 1,4-dioxane and undissolved material
  11. customremoved by filtration
  12. additionThe filtrate was diluted with water
  13. filtrationThe ensuing solid was filtered through a Buchner funnel
  14. washwashed three times with 1 ml water
  15. customThe product was dried in air for a short time

Sources & evidence

ORD record
ord-72010884bc8643be9ac1806c17c4a776
Source dataset
uspto-grants-2002_10
Patent number
US06468990B1

Reaction notes

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