Ammonia methanol → 6-Methoxy-2,3-dihydro-1H-isoindol-1-one

HRID 1727400Notes

Reaction equation

HRID 1727400 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:4]=1[C:5](OC)=[O:6].[NH3:15].CO>CO>[CH3:14][O:13][C:10]1[CH:9]=[C:4]2[C:3]([CH2:2][NH:15][C:5]2=[O:6])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 53407594Methyl 2-(bromomethyl)-5-methoxybenzoate

Product 1

HCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-oneYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

A solution of methyl 2-(bromomethyl)-5-methoxybenzoate ((75), 5.0 g, 19.3 mmol) in MeOH was placed in pressure flask and to it ammonia/methanol (2M, 30 ml) was added. Resulting mixture was stirred at 125° C. for 2 hr. The solvent and excess NH3 was removed in vacuo and the residue was triturated with Hexane/EtOAc (1:2 ratio). The compound was filtrated under vacuum and air-dried for 2 hr to give the title compound (2.51 g, 65%) as a pale yellow solid. The filtrated was concentrated and purified on silica gel (Hexane/EtOAc/MeOH 3:1:0.5 ratio) to yield another 270 mg of desired compound. Combined yield was 86%. MS (ES) m/z 164.1.

Workup

  1. additionwas added
  2. customResulting mixture
  3. customThe solvent and excess NH3 was removed in vacuo
  4. customthe residue was triturated with Hexane/EtOAc (1:2 ratio)
  5. filtrationThe compound was filtrated under vacuum
  6. customair-dried for 2 hr

Sources & evidence

ORD record
ord-b7f49274fcf34097a920a8a339f9fb10
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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