Ammonia → 5-methoxy-2,3-dihydro-1H-isoindol-1-one

HRID 2427501Notes

Reaction equation

HRID 2427501 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12]Br.[NH3:15]>CO.[NH4+].[OH-]>[CH3:11][O:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:2])[NH:15][CH2:12]2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoate

Product 1

HCID 220647195-methoxy-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

2-Bromomethyl-4-methoxy-benzoic acid methyl ester, 2% ammonia in MeOH (4 mL) and NH4OH (1.5 mL) were stirred for at 18 hours at room temperature. The reaction was partitioned between CH2Cl2 and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford a white solid (151 mg). 1H NMR (300 MHz, CDCl3): δ 7.80 (d, 2H), 7.02 (dd, 1H), 6.97 (s, 1H), 4.44 (s, 2H), 3.90 (s, 3H).

Workup

  1. customThe reaction was partitioned between CH2Cl2 and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8aed4c9f09d84df896b1536efdbcb791
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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