Methyl iodide → HCID 21698922, compound

HRID 1597186Notes

Reaction equation

HRID 1597186 reaction equation
[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[C:11]([N+:24]([O-:26])=[O:25])[C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:29]I>CN(C)C=O>[F:1][C:2]1[C:12]([N:13]2[C:21](=[O:22])[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]2=[O:23])=[C:11]([N+:24]([O-:26])=[O:25])[C:5]2[N:6]([CH3:29])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21698918HCID 21698918, compound

Product 1

HCID 21698922HCID 21698922, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-[7-Fluoro-5-nitro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (1.3 g) was dissolved in anhydrous dimethylformamide (15 ml) and was slowly added to a stirred suspension of sodium hydride (0.11 g) in dimethylformamide (15 ml) under ice cooling. Solution was stirred for 0.5 hr followed by the addition of methyl iodide (2.03 g). After stirring for 2 hr at ambient temperature, solution was added to ice-water and product was isolated by partitioning with ethyl acetate. Purification by column chromatography on silica gel in hexane-ethyl acetate (3:1) afforded the title compound (0.58 g).

Workup

  1. stirringAfter stirring for 2 hr at ambient temperature
  2. customproduct was isolated
  3. customby partitioning with ethyl acetate
  4. customPurification by column chromatography on silica gel in hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-bbc0f1b4967647df8f4fd2bf0956e5c6
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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