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

HRID 1640263Notes

Reaction equation

HRID 1640263 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 the mixture was stirred for one day at RT. The reaction mixture was evaporated down using the rotary evaporator, combined with 20 mL of 4N aqueous hydrochloric acid and stirred for 1 h at RT. While cooling with ice, 45 mL of a 4N aqueous 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 a 4N aqueous 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-e7ce1094e322458a9400a24b1889de09
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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