Methyl iodide → 6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1045363Notes

Reaction equation

HRID 1045363 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].CI.[C:17](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[N:11]([CH3:17])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 36419566-Acetyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 405391446-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one (1 g, 5.23 mmol), methyl iodide (1.13 g, 7.84 mmol) and cesium carbonate (2.55 g, 7.84 mmol) were dissolved in DMF (2 mL). The reaction mixture was irradiated by microwave for 30 minutes at 100° C. The solvent was removed and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.9 g, 84%). 1H NMR (400 MHz, CDCl3): δ 7.63 (s, 1H), 7.60 (d, 1H), 7.01 (d, 1H), 4.70 (s, 2H), 3.42 (s, 3H), 2.60 (s, 3H); MS (ESI) m/z: Calculated for C11H11NO3: 205.1. found: 206.1 (M+H)+.

Workup

  1. customThe reaction mixture was irradiated by microwave for 30 minutes at 100° C
  2. customThe solvent was removed
  3. extractionextracted with dichloromethane
  4. customPurification by silica chromatography (ISCO)

Sources & evidence

ORD record
ord-7ab2d9a2963343aabcc2a81190f2ca72
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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