Hydrochloric Acid → 1-hexyl-5-methoxy-2-methyl-1H-indole-3-acetamide

HRID 1069595Notes

Reaction equation

HRID 1069595 reaction equation
[Al](C)(C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+:13].C([O:16][C:17](=O)[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:20]=1[CH3:36])C.Cl>C(OCC)(=O)C.O>[CH2:30]([N:21]1[C:22]2[C:27](=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:19]([CH2:18][C:17]([NH2:13])=[O:16])=[C:20]1[CH3:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 18425018Trimethylaluminium tolueneHCID 542146911-hexyl-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester

Product 1

HCID 211918951-hexyl-5-methoxy-2-methyl-1H-indole-3-acetamideYield 40.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2M solution of Al(CH3)3/toluene (15 mL, 0.03 mol) was added to 1.61 g (0.03 mol) of ammonium chloride while slowly keeping the temperature at 5-7° C. with an ice-water bath. The bath was removed, the mixture stirred for 0.5 hour and 1.01 g (3.05 mmol) of 1-hexyl-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester was added. After stirring for 16 hours, 10 mL of water was added cautiously and the mixture added to 1N HCl and a large volume of ethyl acetate. The organic layer was separated, washed with water, sodium bicarbonate solution and dried (Na2SO4). After removing the solvent at reduced pressure the residue was crystallized from MeOH/water to give 0.37 g (40% yield) of 1-hexyl-5-methoxy-2-methyl-1H-indole-3-acetamide, mp, 120-121° C.

Workup

  1. customat 5-7° C.
  2. customThe bath was removed
  3. stirringAfter stirring for 16 hours
  4. customThe organic layer was separated
  5. washwashed with water, sodium bicarbonate solution
  6. dry with materialdried (Na2SO4)
  7. customAfter removing the solvent at reduced pressure the residue
  8. customwas crystallized from MeOH/water

Sources & evidence

ORD record
ord-8849e9e6435d401284ee00d3f49e664a
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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