Acetyl chloride → HCID 136132506, compound

HRID 361616Notes

Reaction equation

HRID 361616 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[NH:6][C:5]=1[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>C1COCC1>[C:26]([O:1][N:2]=[CH:3][C:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[NH:6][C:5]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 136365331HCID 136365331, compound

Product 1

HCID 136132506HCID 136132506, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.8 g (3.3 mmol) of methyl 3-(hydroxyiminomethyl)-4,7-dimethylindole-2-carboxylate in 15 ml of anhydrous THF was cooled to 0° C., and then 0.5 ml (3.6 mmol) of triethylamine was added. While the reaction mixture was stirred at 0° C., a solution of 0.25 ml (3.6 mmol) of acetyl chloride in 5 ml of THF was added dropwise over a period of 15 minutes. The reaction mixture was stirred at room temperature for 1 hour and then poured into 100 ml of ice water. The crystals were separated by filtration and dried to provide 0.85 g of yellow crystals.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. customThe crystals were separated by filtration
  3. customdried

Sources & evidence

ORD record
ord-fef9d24464444e45aaed2d573c5a4dd4
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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