Hydrochloric Acid → 6-(Piperidin-4-ylidenemethyl)-1,3-dihydroindol-2-one

HRID 1295585Notes

Reaction equation

HRID 1295585 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21](C(OC)=O)[C:22](OC)=[O:23])=[C:17]([N+:30]([O-])=O)[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Sn].Cl>C(O)C>[NH:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:16]=[C:17]3[C:18]([CH2:21][C:22](=[O:23])[NH:30]3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 86597572Dimethyl 2-[4-(1-tert-butoxycarbonylpiperidin-4-ylidenemethyl)-2-nitrophenyl]malonate

Product 1

HCID 179651476-(Piperidin-4-ylidenemethyl)-1,3-dihydroindol-2-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethyl 2-[4-(1-tert-butoxycarbonylpiperidin-4-ylidenemethyl)-2-nitrophenyl]malonate (1.65 g; 3.7 mmol) was dissolved in ethanol (50 ml), tin powder (1.31 g; 11 g atom) was added followed by conc. hydrochloric acid (10 ml) and the mixture heated at reflux for 3 h before being left to stand at ambient temperature for 18 h. Evaporated to dryness under reduced pressure, water added to the residue and the insoluble material removed by filtration. The filtrate and washings were combined and evaporated to dryness under reduced pressure and this residue extracted with hot methanol. The insoluble materials were further extracted with hot ethanol, the extracts combined and evaporated to dryness under reduced pressure to give the title compound (680 mg; 81%) as a brown foam.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. waitbefore being left
  4. customEvaporated to dryness under reduced pressure, water
  5. additionadded to the residue
  6. customthe insoluble material removed by filtration
  7. customevaporated to dryness under reduced pressure
  8. extractionthis residue extracted with hot methanol
  9. extractionThe insoluble materials were further extracted with hot ethanol
  10. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3a3d40da95814a258da6edf390484da5
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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