Methyl iodide → HCID 13746033, compound

HRID 2290931Notes

Reaction equation

HRID 2290931 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][CH:12]3[CH:8]([C:9](=[O:17])[NH:10][C:11]3=[O:16])[C:7]=2[C:6]([CH3:18])=[CH:5][C:4]=1[O:19][CH3:20].[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][CH:12]3[CH:8]([C:9](=[O:17])[N:10]([CH3:23])[C:11]3=[O:16])[C:7]=2[C:6]([CH3:18])=[CH:5][C:4]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13746030HCID 13746030, compound

Product 1

HCID 13746033HCID 13746033, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3a,4,5,9b-tetrahydro-6,7-dimethoxy-9-methyl-1H-benz[e]isoindole-1,3-(2H)-dione (1.66 g, 6.1 mmole) and dry DMF (28 mL) was stirred under N2 at 0° as a suspension of NaH (60% in oil, washed with hexane, 0.25 g, 6.4 mmole) and DMF (2.8 mL) was added portionwise. The reaction mixture was stirred for 0.5 hour at 0°, and for 0.5 hour at room temperature, then was cooled again at 0° as methyliodide (9.41 mL, 6.6 mmole) was added dropwise. After one hour at 0° and 1.5 hours at room temperature, the reaction mixture was poured onto ice water. The solid was filtered, washed with water, dried (in vacuo) to yield 1.60 g yellow solid (91%), mp 167°-9° C.; M+ 289.

Workup

  1. additionwas added portionwise
  2. waitfor 0.5 hour at room temperature
  3. additionwas added dropwise
  4. waitAfter one hour at 0°
  5. addition1.5 hours at room temperature, the reaction mixture was poured onto ice water
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried (in vacuo)

Sources & evidence

ORD record
ord-9b2bf0ac0bf245109f4e9df0c5348c67
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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