2-ethyl-1H-indole → 2-ethyl-2,3-dihydro-1H-indole

HRID 74590Notes

Reaction equation

HRID 74590 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:2].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 38016182-ethyl-1H-indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 107731212-ethyl-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.66 g (4.2 mmol) 2-ethyl-1H-indole in 10 mL acetic acid were mixed with 1.3 g (20 mmol) sodium cyanoborohydride and stirred for one day at RT. The reaction mixture was evaporated down using the rotary evaporator, combined with 20 mL aqueous 4N hydrochloric acid and stirred for 1 h at RT. While cooling with ice 45 mL of an aqueous 4N sodium hydroxide solution were then added and the mixture was extracted with ethyl acetate. The organic phase was dried on sodium sulphate, filtered, evaporated down and the residue was dried in vacuo.

Workup

  1. customThe reaction mixture was evaporated down
  2. customthe rotary evaporator
  3. stirringstirred for 1 h at RT
  4. temperatureWhile cooling with ice 45 mL of an aqueous 4N sodium hydroxide solution
  5. additionwere then added
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe organic phase was dried on sodium sulphate
  8. filtrationfiltered
  9. customevaporated down
  10. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-165e068de69048f2b2016b2a8ecdc74d
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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