4-Amino-1-butanol → 2-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione

HRID 1504070Notes

Reaction equation

HRID 1504070 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])N1C(OCC)=O>C1COCC1>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][N:1]1[C:8](=[O:7])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]

Participants

4

Reactant 2

HCID 258684-Amino-1-butanolHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 111175282-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-aminobutan-1-ol (18 g, 201.94 mmol, 1.00 equiv), ethyl 1,3-dioxo-2,3-dihydro-1H-isoindole-2-carboxylate (44.5 g, 203.02 mmol, 1.01 equiv) and TEA (28 g, 276.71 mmol, 1.37 equiv) in 500 mL of THF was heated to reflux overnight. The reaction mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with PE/EtOAc (10:1 to 1:1) to give 30 g (68%) of 2-(4-hydroxybutyl)-2,3-dihydro-1H-isoindole-1,3-dione as a white solid. MS (ES): m/z 220 (M+H)+.

Workup

  1. temperatureto reflux overnight
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solids were filtered out
  7. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a2e299f1e8e84a29b2dd541793573257
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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