Hydrochloric Acid → HCID 12958510, compound

HRID 2426871Notes

Reaction equation

HRID 2426871 reaction equation
C([N:8]1[CH2:12][CH:11]2[C:13](=[O:23])[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:16])[CH:10]2[CH2:9]1)C1C=CC=CC=1.Cl.[OH-].[Na+]>C(O)C.[Pd]>[C:17]1([N:14]2[C:13](=[O:23])[CH:11]3[CH:10]([CH2:9][NH:8][CH2:12]3)[C:15]2=[O:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 356437NSC612200

Product 1

HCID 12958510HCID 12958510, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-benzyl-2-phenyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione, freed of its hydrochloride beforehand by treatment with 4 N sodium hydroxide (93.2 g; 304 mmol), in absolute ethanol (1200 ml) is placed in a 5000 ml autoclave and palladium-on-charcoal at 5% (11 g) is then added. After having purged with nitrogen, the autoclave is placed under 64 bar of hydrogen at 70° C. for 12 hours. After returning to 20° C., the catalyst is filtered off and the filtrate is evaporated under reduced pressure. The compound obtained is triturated in diisopropyl ether (500 ml) and the solid obtained is filtered off, washed with diisopropyl ether and, finally, dried under reduced pressure at constant weight. 2-Phenyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione, (6.6 g; 92%) is isolated, the characteristics of which are as follows:

Workup

  1. additionis then added
  2. customAfter having purged with nitrogen
  3. customAfter returning to 20° C.
  4. filtrationthe catalyst is filtered off
  5. customthe filtrate is evaporated under reduced pressure
  6. customThe compound obtained
  7. customis triturated in diisopropyl ether (500 ml)
  8. customthe solid obtained
  9. filtrationis filtered off
  10. washwashed with diisopropyl ether
  11. customfinally, dried under reduced pressure at constant weight

Sources & evidence

ORD record
ord-90be4313ea0d4889b7b089a3677efef4
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

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