Acetic Anhydride → N-(1-ethyl-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamide

HRID 1181568Notes

Reaction equation

HRID 1181568 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:15])([CH3:14])[C:7](=[O:13])[N:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[CH2:11]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:16](=[O:18])[CH3:17])[CH:10]=2)[C:6]([CH3:14])([CH3:15])[C:7]1=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 69068988HCID 69068988, compound

Product 1

HCID 69070576N-(1-ethyl-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamideYield 91%

Procedure

A solution of 6-amino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one (5.05 g, 24.72 mmol) in acetic anhydride (80 ml) was stirred at room temperature for 4 h. The mixture was poured onto ice water (150 ml), allowed to warm to room temperature and was stirred again for 2 h. After extraction with ethyl acetate (3×100 ml), the combined organic layers were washed with sat. NaHCO3-solution (3×100 ml), brine (100 ml) and dried over sodium sulfate. After removal of the solvent the crude product was purified by column chromatography on silica gel (ethyl acetate/n-heptane 1:1) yielding 5.6 g (91%) N-(1-ethyl-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamide as light yellow solid.

Workup

  1. additionThe mixture was poured onto ice water (150 ml)
  2. extractionAfter extraction with ethyl acetate (3×100 ml)
  3. washthe combined organic layers were washed with sat. NaHCO3-solution (3×100 ml), brine (100 ml)
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent the crude product
  6. customwas purified by column chromatography on silica gel (ethyl acetate/n-heptane 1:1)

Sources & evidence

ORD record
ord-93f1592117ff4cbbbc2a8d2b8d718bf1
Source dataset
uspto-grants-2007_10
Patent number
US07285569B2

Reaction notes

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