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

HRID 2279757Notes

Reaction equation

HRID 2279757 reaction equation
[CH3:1][NH2:2].C(O)C.Br[CH2:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:9]=1[C:10](OC)=[O:11]>C1COCC1>[CH3:1][N:2]1[CH2:7][C:8]2[C:9](=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:16][CH:17]=2)[C:10]1=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate2×

Product 1

HCID 587485312-Methyl-7-nitro-2,3-dihydro-1H-isoindol-1-oneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methylamine in ethanol (10 mL, 80 mmol, 8M solution in ethanol) was added to a solution of methyl 2-(bromomethyl)-6-nitrobenzoate (Compound 17G, 8.1 g, 29.6 mmol) in THF (30 mL). After stirring for 2 h the reaction mixture was concentrated to dryness and water (30 mL) was added with rapid stirring. The solids produced were isolated by filtration and dried to give 4.35 g of 2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (yield: 78%). 1H NMR (CDCl3, 400 MHz): δ 3.21 (s, 3H), 4.44 (s, 2H), 7.64 (m, 2H), 7.73-7.74 (m, 1H).

Workup

  1. concentrationwas concentrated to dryness and water (30 mL)
  2. additionwas added with rapid stirring
  3. customThe solids produced
  4. customwere isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-da85a29eed7449fb8a14f2aee173512c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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