Hydrochloric Acid → 1-butylindole-3-carboxylic Acid

HRID 129565Notes

Reaction equation

HRID 129565 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]1.I[CH2:16][CH2:17][CH2:18][CH3:19].Cl>CN(C=O)C>[CH2:16]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 103762901-butylindole-3-carboxylic AcidYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (34.1 g, 1.42 mol) in 300 mL of DMF was stirred in an ice/methanol bath and a solution of 3-indolecarboxylic acid (55.0 g, 0,374 mol) in 250 mL DMF was added dropwise over 45 minutes. The mixture was stirred for 30 minutes and then 100 mL of additional DMF was added. The mixture was cooled to 0° C. and 1-iodobutane (8.79 g, 40.8 mL, 0.359 mol) was added. The mixture was stirred for approximately 12 hours. The mixture was then poured in 2.0 L of ice water, acidified with 1N hydrochloric acid, extracted 3 times with ethyl acetate, washed twice with water and then dried over magnesium sulfate. The mixture was concentrated and the residue mixed with diethylether. Filtration gave 1-butylindole-3-carboxylic acid (62.74 g, 0.309 mol) as a white powder.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringThe mixture was stirred for approximately 12 hours
  3. extractionextracted 3 times with ethyl acetate
  4. washwashed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe mixture was concentrated
  7. additionthe residue mixed with diethylether
  8. filtrationFiltration

Sources & evidence

ORD record
ord-f10061a6be884cefb5db8cd6941f284e
Source dataset
uspto-grants-1995_11
Patent number
US05468867

Reaction notes

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