1-benzyl-2,3-dihydroindole-5-carbaldehyde → 5-Methylindoline

HRID 1108476Notes

Reaction equation

HRID 1108476 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C>[CH3:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH2:9][CH2:10]2

Participants

4

Reactant 2

HCID 9275671-benzyl-2,3-dihydroindole-5-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 140236795-MethylindolineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 200 mλ pressure resistant reactor (autoclave) equipped with a stirrer, 20 g (0.084 mol) of 1-benzyl-5-formylindoline and 100 mλ of ethanol were charged, and the interior of the reactor was flushed with nitrogen. 2 g of 10% Pd/C was introduced, and the reactor was closed, whereupon hydrogen was introduced from a hydrogen supply pipe and reacted at 80° C. for 6 hours while adjusting the initial pressure of hydrogen in the reactor to be 6 2 kg/cm. Upon confirming the ceasing of absorption of hydrogen, the reaction was terminated. Then, the reaction solution was cooled to room temperature, and the hydrogen was released, and the palladium catalyst (10% Pd/C) was collected by filtration, and ethanol was distilled off under reduced pressure to obtain a colorless liquid as the residue. The obtained liquid was subjected to vacuum distillation to obtain 9.5 g of 5-methylindoline having a boiling point of from 56 to 57° C./0.3 mmHg. The yield was 85% (based on 1-benzyl-5-formylindoline).

Workup

  1. customInto a 200 mλ pressure resistant reactor (autoclave) equipped with a stirrer
  2. customthe interior of the reactor was flushed with nitrogen
  3. addition2 g of 10% Pd/C was introduced
  4. customthe reactor was closed, whereupon hydrogen
  5. additionwas introduced from a hydrogen supply pipe
  6. customreacted at 80° C. for 6 hours
  7. customthe ceasing of absorption of hydrogen
  8. customthe reaction was terminated
  9. filtrationthe palladium catalyst (10% Pd/C) was collected by filtration, and ethanol
  10. distillationwas distilled off under reduced pressure
  11. customto obtain a colorless liquid as the residue
  12. distillationThe obtained liquid was subjected to vacuum distillation

Sources & evidence

ORD record
ord-7efaae340d6b472aaadce8a2753236ad
Source dataset
uspto-grants-2000_05
Patent number
US06066744

Reaction notes

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