Sulfuric Acid → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal

HRID 436633

Reaction equation

HRID 436633 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6][CH2:7][CH2:8][CH:9](OCC)[O:10]CC)[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12.S(=O)(=O)(O)O>C(OC(OCC)CCCN)C>[C:4]1(=[O:16])[N:5]([CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[C:1](=[O:21])[C:2]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:3]12

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dione

Product 1

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal

Reagents, catalysts & solvents 1

HCID 806724,4-DiethoxybutylamineSolvent

Procedure

Protect the amino function in 4,4-diethoxybutylamine by conversion thereof to a phthalimido function. Hydrolyze the resultant 1-phthalimido-4,4-diethoxybutane with 1N aqueous sulfuric acid at 25° C to obtain 4-phthalimidobutanal. Subject the compound to reductive amination using ammonium chloride and sodium cyanoborohydride in aqueous methanol at 25° C to obtain 4-phthalimidobutylamine.

Workup

  1. customat 25° C

Sources & evidence

ORD record
ord-3a306dee696a447e8932b041cbcf69d2
Source dataset
uspto-grants-1977_02
Patent number
US04009328

Linked notes

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