Dimethylformamide → 4-Methoxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

HRID 511440Notes

Reaction equation

HRID 511440 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:15])[C:6]2=[O:14].[C:16](=O)([O-])[O-].[K+].[K+].CN(C=O)C.CI>CCOC(C)=O>[CH3:16][O:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:15])[C:6]2=[O:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 598492054-Hydroxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one2×

Product 1

HCID 598491794-Methoxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-Hydroxy-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 205C, 50.0 mg, 0.240 mmol), potassium carbonate (49.8 mg, 0.360 mmol) in DMF (2 mL, 20 mmol) was treated with methyl iodide (22.4 μL, 0.360 mmol) and allowed to stir at room temperature overnight. The reaction was poured into EtOAc and washed with water and brine and the crude material was purified using an ISCO Combiflash unit (MeOH in DCM: 0-1%) to obtain the title product as a solid. (27 mg, 50% yield). 1H NMR (400 MHz, CD3OD) δ=3.17 (s, 3 H), 4.02 (s, 3 H), 4.44 (s, 2 H), 7.27 (d, J=8.8 Hz, 1 H), 7.94 (d, J=8.8 Hz, 1 H). MS (ES+): m/z 223.19 (100) [MH+]; HPLC: tR=0.76 min (UPLC, analytical).

Workup

  1. washwashed with water and brine
  2. customthe crude material was purified

Sources & evidence

ORD record
ord-32f7750b2ee04661a4d548ace851642e
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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