Hexane → 1H-Indole-4-carbonyl chloride

HRID 2051196Notes

Reaction equation

HRID 2051196 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(Cl)(=O)C([Cl:16])=O.CCCCCC>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]([Cl:16])=[O:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 65578Oxalyl chlorideHCID 595229Indole-4-carboxylic acid

Product 1

HCID 144031811H-Indole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

32.2 g (0.2 M) dry indol-4-yl carboxylic acid are suspended in 150 ml absolute methylene chloride, 26 ml (0.3 M) oxalyl chloride are added to the stirred mixture at 20° over 30 minutes. Gas evolution results. The mixture is stirred for 31/2 hours at 20° C. 150 ml Hexane are added. The mixture is stirred for another 20 minutes and the resultant heading compound filtered off, washed with methylene chloride/hexane 1:1 dried at 20° in a vacuum to give beige crystals, which are used further without purification.

Workup

  1. customGas evolution results
  2. stirringThe mixture is stirred for another 20 minutes
  3. filtrationfiltered off
  4. washwashed with methylene chloride/hexane 1:1
  5. customdried at 20° in a vacuum
  6. customto give beige crystals, which
  7. customare used further without purification

Sources & evidence

ORD record
ord-97e16f29c6e042b1970130ab11bce80a
Source dataset
uspto-grants-1991_05
Patent number
US05017582

Reaction notes

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