HCID 12546902, compound → Phthalimide

HRID 1856300Notes

Reaction equation

HRID 1856300 reaction equation
NCCC(NC1C(C)=CC=CC=1CC)=O.BrCCC(NC1C(C)=CC(OCCC)=CC=1C)=O.[C:34]1(=[O:44])[NH:38][C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12.[K]>CN(C)C=O>[C:34]1(=[O:44])[NH:38][C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12

Participants

5

Reactant 3

HCID 12546902HCID 12546902, compoundHCID 125469113-Amino-2'-ethyl-6'-methylpropionanilideHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared analogously to 3-amino-2'-ethyl-6'-methylpropionanilide of Example 11B from 15.7 g 3-bromo-2',6'-dimethyl-4'-propoxypropionanilide and 10.2 g potassium phthalimide in 50 ml dimethyl formamide. The intermediate phthalimide derivative was obtained in 88% yield. It was decomposed by being suspended in 250 ml 95% alcohol with addition of 4 ml of 64% hydrazine and refluxing for 90 min. A hydrochloride was prepared from the obtained base; m.p. 208°-210.5° C. Calcd. for C14H23ClN2O2 : C 58.6, H 8.08, Cl 12.4, N 9.77. Found: C 58.8, H 8.20, Cl 12.3, N 9.96.

Sources & evidence

ORD record
ord-34c016421d8f48929dbbc57341184ca6
Source dataset
uspto-grants-1980_08
Patent number
US04218477

Reaction notes

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