N-Carbethoxyphthalimide → 2-(4,4-Diethoxybutyl)isoindoline-1,3-dione

HRID 1003697Notes

Reaction equation

HRID 1003697 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][CH2:6][CH2:7][NH2:8])[CH3:2].C(OC(N1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])=O)C>O1CCCC1>[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][CH2:7][N:8]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])[CH3:11]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 806724,4-Diethoxybutylamine

Product 1

HCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dioneYield 104.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-aminobutyraldehyde diethyl acetal (48.5 g, 0.3 mol) in tetrahydrofuran (60 ml) was added dropwise to a stirred slurry of N-(ethoxycarbonyl) phthalimide (65.93 g, 0.3 mol) in tetrahydrofuran (250 ml) at 0° C. After stirring at 0° C. for 0.16 h and at room temperature for 18 h the solvent was removed in vacuo and the residue distilled at 1 mmHg to remove the ethyl carbamate by-product. The residual brown oil was allowed to cool to afford the title compound (91 g, 93%).

Workup

  1. customwas removed in vacuo
  2. distillationthe residue distilled at 1 mmHg
  3. customto remove the ethyl carbamate by-product
  4. temperatureto cool

Sources & evidence

ORD record
ord-b7ebee8c1b7d419182063dd24fd4fa1d
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

Loading…