Methanol → HCID 67253776, compound

HRID 511366Notes

Reaction equation

HRID 511366 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:14])[NH:3]1.[H-].[Na+].[CH3:18]O.IC>C1COCC1.O>[CH3:18][N:3]1[C:2]([CH3:15])([CH3:1])[C:10]2[C:5](=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 670953413,3-Dimethyl-7-nitro-2,3-dihydro-isoindol-1-one2×

Product 1

HCID 67253776HCID 67253776, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3-dimethyl-7-nitroisoindolin-1-one (Compound 148C, 100 mg, 0.48 mmol) in THF (5 mL), was treated with 60% NaH (58 mg, 1.44 mmol) and stirred for 15 minutes. Methanol (0.078 mL, 1.92 mmol) and iodomethane (0.12 mL, 1.92 mmol) were added to this solution and stirred at 50° C. overnight. Cold water (3 mL) was added, the reaction mixture was concentrated to remove THF and extracted with EtOAc (3×5 mL). The combined organic layer washed with brine, dried (Na2SO4) and concentrated to provide 70 mg of the title compound (66%). 1H NMR (CDCl3, 600 MHz): δ 1.45 (s, 6H), 3.56 (s, 3H), 7.13 (dd, J=7.8, 84 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 8.02 (d, J=8.4 Hz, 1H).

Workup

  1. stirringstirred at 50° C. overnight
  2. concentrationthe reaction mixture was concentrated
  3. customto remove THF
  4. extractionextracted with EtOAc (3×5 mL)
  5. washThe combined organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d5c3fea5a25a4ea7925a64e55540e105
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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