Methylamine → 2-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one

HRID 2382637Notes

Reaction equation

HRID 2382637 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:4]=1[C:5](OC)=[O:6].[CH3:16][NH2:17].C(Cl)Cl.CCOC(C)=O>C1COCC1.CCOC(C)=O>[CH3:16][N:17]1[CH2:2][C:3]2[C:4](=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:11][CH:12]=2)[C:5]1=[O:6]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 21226138Dichloromethane ethylacetateHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

Product 1

HCID 587485312-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, a solution of methyl 2-bromomethyl-6-nitrobenzoate (1.26 g, 4.63 mmol) in THF (13 mL) is treated with 2M soln. of methylamine in THF (14 mL), stirred for 5 h, diluted with EtOAc (100 mL), washed with sat. aqueous solution of NaHCO3 (15 mL) and brine (15 mL), dried (MgSO4), and evaporated. A flash chromatography (30 g of silica gel; CH2Cl2/EtOAc 1:1) gives N-Methyl-7-nitro-2,3-dihydroisoindole-1-one (0.561 g, 2.92 mmol) in 63%. Yellow solid. Rf (CH2Cl2/EtOAC 1:1) 0.46. 1H-NMR (400 MHz, CDCl3) 3.21 (s), 4.44 (s), 7.63-7.69 (m, 2H), 7.70-7.75 (m, 1H).

Workup

  1. washwashed with sat. aqueous solution of NaHCO3 (15 mL) and brine (15 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-7a14e29ad83e4a12b7e45dbc58d8c131
Source dataset
uspto-grants-2012_09
Patent number
US08263590B2

Reaction notes

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