Phthalic Anhydride → 2-[1-(3,4-Dimethoxy-phenyl)-3-hydroxy-propyl]-isoindole-1,3-dione

HRID 1941239Notes

Reaction equation

HRID 1941239 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)[CH2:3][CH2:4][OH:5].[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12>CCOCC>[C:16]1(=[O:21])[N:1]([CH:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[CH2:3][CH2:4][OH:5])[C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 37392353-Amino-3-(3,4-dimethoxyphenyl)propan-1-ol

Product 1

HCID 98409252-[1-(3,4-Dimethoxy-phenyl)-3-hydroxy-propyl]-isoindole-1,3-dioneYield 73.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-amino-3-(3',4'-dimethoxyphenyl)-propan-1-ol (1.11 grams, 5 mmol) and phthalic anhydride (0.74 grams, 5 mmol) were melted together and stirred for 5 minutes. After cooling, a green/yellow glassy semi solid formed which was stirred in ether to afford 1.62 g (95%) of crude product as a white solid. The crude product was purified by flash chromatography (silica gel, 40% ethyl acetate/methylene chloride) to afford 1.25 grams (73%) of product as a white solid. 1H NMR (CDCl3)δ7.85-7.63 (m, 4H), 7.18-7.07 (m , 2H), 6.86-6.76 (m, 1H), 5.62-5.49(m, 1H), 3.88 (s, 3H), 3.85 (s, 3H), 3.79-3.63 (m, 2H), 2.89-2.71 (m, 1H), 2.64-2.47 (m, 1H), 1.87-1.73 (br m, 1H). 13C NMR (CDCl3)δ168.5, 148.8, 148.6, 133.9, 131.8, 131.7, 123.2, 120.7, 111.6, 110.8, 59.8, 55.0, 55.8, 51.4, 33.9. Anal. Calcd. for C19 H19NO5. Theoretical: C, 66.85; H, 5.61 ;N, 4.10. Found: C, 66.70; H, 5.60; N, 4.06. HPLC 100%.

Workup

  1. temperatureAfter cooling
  2. customa green/yellow glassy semi solid formed which
  3. customto afford 1.62 g (95%) of crude product as a white solid
  4. customThe crude product was purified by flash chromatography (silica gel, 40% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-2949209242fc4d33b30e60f4a3477de5
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

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