Hydrochloric Acid → HCID 21460516, compound

HRID 1941248Notes

Reaction equation

HRID 1941248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])[CH2:12][CH2:13][OH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:26]I.[H-].[Na+].Cl>C1COCC1.[NH4+].[Cl-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:15]2[C:16](=[O:25])[C:17]3=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]3[C:19]2=[O:20])[CH2:12][CH2:13][O:14][CH3:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98409252-[1-(3,4-Dimethoxy-phenyl)-3-hydroxy-propyl]-isoindole-1,3-dione

Product 1

HCID 21460516HCID 21460516, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3',4'-dimethoxyphenyl)-3-phthalimido-1-propanol (1.02 grams, 2.99 mmol) and methyl iodide (0.37 mL, 5.94 mmol) in THF (10 mL) at room temperature, was added NaH (358 mg, 60%, 8.95 mmol). The mixture was stirred at room temperature for 45 minutes, and then was refluxed for 2 h. To the cooled mixture was added a few drops of NH4Cl, then HCl (1N, 25 mL). The organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (25 mL), and dried over magnesium sulfate. Removal of solvent and chromatography (silica gel 100 grams, 1:5 EtOAc:hexane) gave 3-(3',4'-dimethoxyphenyl)-1-methoxy-3-phthalimidopropane as a white solid, (750 mg, 71% yield): mp, 91.5°-92.5° C.; 1H NMR (CDCl3)δ2.50-2.59 (m, 1H, CHH), 2.70-2.86 (m, 1H, CHH), 3.27 (s, 3H, CH3), 3.39 (t, J=6 Hz, 2H, CH2), 3.85 (s, 3H, CH3), 3.88 (s, 3H, CH3), 5.49 (dd, J=6.8, 9.2 Hz, 1H, NCH), 6.81 (d, J=8 Hz, 1H, Ar), 7.11-7.15 (m, 2H, Ar), 7.67-7.72 (m, 2H, Ar), 7.77-7.83 (m, 2H, Ar); 13C NMR (CDCl3)δ31.29, 51.93, 55.80, 58.69, 69.64, 110.84, 115.56, 120.62, 123.12, 131.90, 1332.03, 133.84, 148.58, 148.81, 168.38; Anal Calcd for C20H21NO5 : C, 67.59; H, 5.96; N, 3.94. Found: C, 67.54; H, 5.97; N, 3.84.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic layers were washed with brine (25 mL)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent and chromatography (silica gel 100 grams, 1:5 EtOAc:hexane)

Sources & evidence

ORD record
ord-6f3b7c23aa404eac927c9dacd76b6a9a
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

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