Acetic Anhydride → HCID 69073814, compound

HRID 2374483Notes

Reaction equation

HRID 2374483 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[C:6](=[O:14])[C:5]2([CH2:17][CH3:18])[CH2:15][CH3:16].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[CH2:15]([C:5]1([CH2:17][CH3:18])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:19](=[O:21])[CH3:20])[CH:3]=2)[N:7]([CH:11]([CH3:12])[CH3:13])[C:6]1=[O:14])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 69065503HCID 69065503, compound

Product 1

HCID 69073814HCID 69073814, compoundYield 91%

Procedure

A solution of 5-amino-3,3-diethyl-1-isopropyl-1,3-dihydro-indol-2-one (9.7 g, 39.37 mmol) in acetic anhydride (57 ml) was stirred at room temperature for 4 h. The mixture was poured into ice water, allowed to warm to room temperature and was stirred again for 2 h. After extraction with ethyl acetate, the combined organic layers were washed with aqueous NaOH solution (1M) and brine and dried over sodium sulfate. After removal of the solvent the crude product was triturated with iso-hexane to yield 10.4 g N-(3,3-Diethyl-1-isopropyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (36.06 mmol, 91%)

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe combined organic layers were washed with aqueous NaOH solution (1M) and brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent the crude product
  5. customwas triturated with iso-hexane

Sources & evidence

ORD record
ord-a55876c1fe744773b5f19d4a295b0153
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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