Benzylamine → HCID 12435486, compound

HRID 1196571Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5](Cl)=[O:6])[CH3:2].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([NH:18][C:5](=[O:6])[CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 19898726Diethoxyacetyl chloride

Product 1

HCID 12435486HCID 12435486, compound

Procedure

Ethyl diethoxyacetate (Ex. Fluka) (25 g) was added to sodium hydroxide (5.68 g) in ethanol (60 ml) and water (30 ml). After heating under reflux for 5 hours the solvents were removed at reduced pressure and the residue dried in vacuo to give sodium diethoxyacetate (23.2 g). The salt was then converted to diethoxyacetyl chloride and reacted with benzylamine to give N-benzyl diethoxyacetamide which was cyclised with conc. sulphuric acid according to Fukumi and Hideshi, Heterocycles, 9, 1197 (1978) to give 3-hydroxyisoquinoline.

Sources & evidence

ORD record: ord-1010de09e3ab4a09a58e340b0c33b324
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05114940

Reaction notes

Loading…