Acetyl chloride → HCID 11131690, compound

HRID 982513Notes

Reaction equation

HRID 982513 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH3:12])[CH3:2].[C:13](Cl)(=O)[CH3:14].C(O[C:21](=O)[CH3:22])(=O)C.[OH-].[Na+]>O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:4]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:21][CH3:22])[C:13]=2[CH3:14])=[CH2:12])=[C:4]1[CH3:12])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 1704321H-Indole, 1-ethyl-2-methyl-

Product 1

HCID 11131690HCID 11131690, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
51 °C

Procedure

A mixture of 1-ethyl-2-methylindole (15.9 g, 0.1 mole), acetyl chloride (2.0 g, 0.025 mole) and acetic anhydride (15 ml) was stirred at 50-52° C. for 8 hours. Then, the reaction mixture was cooled to room temperature and poured into ice, water and sodium hydroxide (10%, 50 ml). After stirring for 20 minutes, the precipitated solid was filtered off, washed with water, refluxed with methanol for 1 hour and cooled. The solid was filtered, washed with methanol and dried. Yield of the product: 16.5g (96%), pale yellow powder, m.p.: 179-182° C. IR(KBr) spectrum was identical to that of the product in Example 1.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. stirringAfter stirring for 20 minutes
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with water
  5. temperaturerefluxed with methanol for 1 hour
  6. temperaturecooled
  7. filtrationThe solid was filtered
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-67568e52d5bb4ff2a6a4fd47edec07d7
Source dataset
uspto-grants-1991_02
Patent number
US04996328

Reaction notes

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