Methyl iodide → 6-Methoxy-3,3,14-trimethyl-13-nitro-3,14-dihydro-7H-benzo[b]pyrano-[3,2-h]acridin-7-one

HRID 478691Notes

Reaction equation

HRID 478691 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:28][C:27]([CH3:30])([CH3:29])[CH:26]=[CH:25][C:6]2=[C:7]2[C:16]=1[C:15](=[O:17])[C:14]1[CH:13]=[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]3=[C:10]([N+:22]([O-:24])=[O:23])[C:9]=1[NH:8]2.[H-].[Na+].I[CH3:34]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:28][C:27]([CH3:30])([CH3:29])[CH:26]=[CH:25][C:6]2=[C:7]2[C:16]=1[C:15](=[O:17])[C:14]1[CH:13]=[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]3=[C:10]([N+:22]([O-:24])=[O:23])[C:9]=1[N:8]2[CH3:34]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 220645196-Methoxy-3,3-dimethyl-13-nitro-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]-acridin-7-one

Product 1

HCID 220645286-Methoxy-3,3,14-trimethyl-13-nitro-3,14-dihydro-7H-benzo[b]pyrano-[3,2-h]acridin-7-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg of the compound obtained in Step 5 in 30 ml of dimethylformamide there are added 1.48 g of sodium hydride and then 1.8 ml of iodomethane. The reaction mixture is refluxed, under argon, for 3 days, and is then slowly hydrolysed by the addition of ice. The precipitate formed is filtered off and then dried and is chromatographed over silica gel (dichloromethane/methanol: gradient from 0.1 to 0.5%), allowing the expected product to be isolated.

Workup

  1. temperatureThe reaction mixture is refluxed, under argon, for 3 days
  2. additionslowly hydrolysed by the addition of ice
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. customdried
  6. customis chromatographed over silica gel (dichloromethane/methanol: gradient from 0.1 to 0.5%)
  7. customto be isolated

Sources & evidence

ORD record
ord-c03da2a3f2bb46ac9e97cc25fae4c1f9
Source dataset
uspto-grants-2003_11
Patent number
US06642248B2

Reaction notes

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