Phthalimide → Ammonium Hydroxide

HRID 915654Notes

Reaction equation

HRID 915654 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][CH2:38][CH2:39]O.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH4+:5].[OH-:6].[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][CH2:38][CH2:39][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 72922PyripropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 2

HCID 14923Ammonium HydroxideHCID 16640922HCID 16640922, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cool a mixture of phthalimide (0.54 g, 3.7 mmol) and PPh3 (0.95 g, 3.6 mmol) in tetrahydrofuran (5.0 mL) to 0° C. Add a solution of 2-pyridine propanol (0.50 g, 3.7 mmol) and diethyl azodicarboxylate (0.60 mL, 3.8 mmol) in tetrahydrofuran (5.0 mL) dropwise over 4 minutes. After 4 hours, concentrate the reaction mixture, redissolve in diethyl ether (50 mL) and filter. Concentrate the filtrate. Perform flash chromatography on silica gel eluting with 20% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH solution in methylene chloride to afford 2-(3-pyridin-2-yl-propyl)isoindole-1,3-dione as a red oil which is used without further purification.

Workup

  1. temperatureCool
  2. concentrationconcentrate the reaction mixture
  3. dissolutionredissolve in diethyl ether (50 mL)
  4. filtrationfilter
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-9734e2b1d3934030aba4b0ab1f9fa195
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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