Isopropyl iodide → HCID 69074084, compound

HRID 2374481Notes

Reaction equation

HRID 2374481 reaction equation
[CH2:1]([C:3]1([CH2:16][CH3:17])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][C:4]1=[O:15])[CH3:2].[H-].[Na+].I[CH:21]([CH3:23])[CH3:22]>CN(C)C=O>[CH2:16]([C:3]1([CH2:1][CH3:2])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]([CH:21]([CH3:23])[CH3:22])[C:4]1=[O:15])[CH3:17]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 13835066HCID 13835066, compound

Product 1

HCID 69074084HCID 69074084, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3,3-diethyl-5-nitro-1,3-dihydro-indol-2-one (11.7 g, 49.95 mmol) in anhydrous N,N-dimethylformamide (DMF) (60 ml) was treated with sodium hydride (1.558 g, 64.93 mmol). The resulting suspension was stirred for 1 h at 60° C. A solution of 2-iodo-propane (4.99 ml, 8.49 g, 49.95 mmol) was added. The mixture was kept at 60° C. for further 3 h, allowed to cool to room temperature poured into ice water. The precipitate was filtered off, washed with water and dried to yield 12.6 g 3,3-diethyl-1-isopropyl-5-nitro-1,3-dihydro-indol-2-one (45.60 mmol, 91%)

Workup

  1. waitThe mixture was kept at 60° C. for further 3 h
  2. temperatureto cool to room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-39475c2e46a04d7c839fcfcbaf33ef66
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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