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

HRID 604285Notes

Reaction equation

HRID 604285 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[CH2:15]Br.[CH3:18][NH2:19]>C1COCC1>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]2[C:5]=1[CH2:15][N:19]([CH3:18])[C:3]2=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59849200HCID 59849200, compound

Product 1

HCID 598491794-Methoxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature, a solution of 2-Bromomethyl-3-methoxy-6-nitro-benzoic acid methyl ester (crude 7.0 g, 18.2 mmol) in 46 mL of THF is treated with 2M solution of methylamine in THF (27.3 mL, 54.6 mmol), and the mixture is stirred for 4 hours at the room temperature. The reaction mixture is quenched with a saturated ammonium chloride solution and partitioned between ethyl acetate. The organic layer is washed with brine and then dried over Na2SO4 following concentrated to give 4-Methoxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (3.1 g) as orange solid in 77% yields (2 steps). 1H-NMR (400 MHz, δ, ppm) CDCl3: 3.19 (s, 3H), 3.99 (s, 3H), 4.32 (s, 2H), 7.0 (d, 1H), 7.89 (d, 1H).

Workup

  1. customThe reaction mixture is quenched with a saturated ammonium chloride solution
  2. custompartitioned between ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4 following
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-16013cadca10482a8a506ba37b891bad
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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