Pyridine → HCID 10920996, compound

HRID 431801Notes

Reaction equation

HRID 431801 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.N1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O1CCCC1.C(Cl)(=O)CCCC>O>[CH2:11]([C:10]1[NH:1][C:2]2[C:3]([CH:8]=1)=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7242O-ToluidineHCID 8028TetrahydrofuranHCID 61186Valeryl chloride

Product 1

HCID 10920996HCID 10920996, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

o-Toluidine (55 g) was mixed with 100 ml dry pyridine and 200 ml dry tetrahydrofuran in a 1-L 3-necked round bottom flask fitted with a Trubore stirrer, thermometer and a dropping funnel, under nitrogen. Then, with cooling in a refrigerated bath, valeryl chloride (60.3 g) was added dropwise over 1 hour. The mixture was stirred for another hour at room temperature and then poured onto 500 g ice and water. The precipitate was washed repeatedly with water on a Buchner funnel. The precipitate (88.9 g, 93%) was cyclized according to Verley and Bedure, 1925, Bull. Soc. Chim. Fr. (37): 190 to afford 2-n-butyl indole (67.4 g, 84%) as a very slightly yellow oil.

Workup

  1. customfitted with a Trubore stirrer
  2. temperatureThen, with cooling in a refrigerated bath
  3. washThe precipitate was washed repeatedly with water on a Buchner funnel

Sources & evidence

ORD record
ord-b4db60736e814859a8242a2d3dca4082
Source dataset
uspto-grants-2003_12
Patent number
US06660763B2

Reaction notes

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