1-Butanol → Butyl (5,6-dichloro-1H-indol-3-yl)acetate

HRID 1382120Notes

Reaction equation

HRID 1382120 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10]N)[CH:6]=[CH:7][C:8]=1[Cl:9].C[CH:13](C)[CH2:14][CH2:15][C:16]([OH:18])=[O:17].[CH2:20]([OH:24])[CH2:21][CH2:22][CH3:23].[OH-].[Na+]>O>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]2[C:4]=1[C:14]([CH2:15][C:16]([O:18][CH3:20])=[O:17])=[CH:13][NH:10]2.[Cl:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[Cl:2])[NH:10][CH:23]=[C:22]2[CH2:21][C:20]([O:17][CH2:16][CH2:15][CH2:14][CH3:13])=[O:24]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 12587Isocaproic acidHCID 14798Sodium HydroxideHCID 3084323(3,4-Dichlorophenyl)hydrazine monohydrochloride

Product 2

HCID 14391419Butyl (5,6-dichloro-1H-indol-3-yl)acetateHCID 14406773Methyl (4,5-dichloro-1H-indol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With 5.81 g of 3,4-dichlorophenylhydrazine hydrochloride was mixed 11.57 g of 4,4-dimethylbutyric acid, and the resulting mixture was sufficiently stirred to obtain a transparent solution, after which 7.64 g of n-butanol was added. The mixed solution was stirred with treating at 110 C. for 1 hour. The reaction solution was cooled to room temperature, diluted with water, and neutralized with a 1N aqueous sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate, and the ethyl acetate phase was washed with distilled water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the oily substance thus obtained was purified by a silica gel column chromatography and a silica gel thin-layer chromatography to obtain 0.28 g of methyl 4,5-dichloroindole-3-acetate and 0.395 g of n-butyl 5,6-dichloroindole-3-acetate.

Workup

  1. customto obtain a transparent solution
  2. stirringThe mixed solution was stirred
  3. additionwith treating at 110 C
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe ethyl acetate phase was washed with distilled water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation
  8. customthe oily substance thus obtained
  9. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-a31317243d9f464b975019bf3b1c2c42
Source dataset
uspto-grants-1989_02
Patent number
US04806143

Reaction notes

Loading…