2-Methoxyethylamine → 5-Hydroxy-2-(2-methoxy-ethyl)-isoindole-1,3-dione

HRID 431584Notes

Reaction equation

HRID 431584 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:26][O:27][CH2:28][CH2:29][NH2:30]>CN(C)C(=O)C>[OH:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:8])[N:30]([CH2:29][CH2:28][O:27][CH3:26])[C:11]2=[O:13]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 118814-Hydroxyphthalic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 148489615-Hydroxy-2-(2-methoxy-ethyl)-isoindole-1,3-dioneYield 99.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-hydroxyphthalic acid (0.91 mg, 5.0 mmol) and carbonyldiimidazole (0.85 g, 5 mmol) in N,N-dimethylacetamide (3 mL) was stirred at room temperature for 45 min. To this mixture was added 2-methoxyethylamine (0.47 g, 6.0 mmol) and the resulting mixture heated under reflux for 15 min. After cooling to room temperature, the mixture was evaporated and the residue was purified by chromatography (SiO2, CH2Cl2:2N NH3/MeOH 19:1 to 9:1) to afford the title compound (1.1 g, 95%) as a light yellow solid. MS: m/e=220.1 (M−H−).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 15 min
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was evaporated
  5. customthe residue was purified by chromatography (SiO2, CH2Cl2:2N NH3/MeOH 19:1 to 9:1)

Sources & evidence

ORD record
ord-8909ba692ad54330bc8252ca92880559
Source dataset
uspto-grants-2003_12
Patent number
US06660736B2

Reaction notes

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