Water → 1H-Indole, 2-propyl-

HRID 1640252Notes

Reaction equation

HRID 1640252 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])#[C:2][CH2:3][CH2:4][CH3:5].CC(C)([O-])C.[K+].O>CN1CCCC1=O>[CH2:3]([C:2]1[NH:12][C:7]2[C:6]([CH:1]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 109317192-Pent-1-ynylanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 1394151H-Indole, 2-propyl-

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The reaction was carried out under an argon atmosphere. 2.7 g (10 mmol) 2-pent-1-ynyl-phenylamine were added to 2.3 g (20 mmol) potassium tert.butoxide in 50 mL of N-methyl-2-pyrrolidinone and the mixture was stirred overnight at RT. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic phase was dried and evaporated down. The residue was purified on silica gel.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated down
  4. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-8a69e37b84ba4999b8a4bba9bc3cb6dd
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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