5-(2-Aminoethoxy)-2-hydroxybenzamide → 5-[2-(Benzylamino)-ethoxy]-salicylamide

HRID 1462382Notes

Reaction equation

HRID 1462382 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1>[Pd].CO>[CH2:10]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([OH:14])=[CH:7][CH:6]=1)[C:9]1[CH:13]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 230496945-(2-Aminoethoxy)-2-hydroxybenzamide

Product 1

HCID 137544195-[2-(Benzylamino)-ethoxy]-salicylamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 5-(2-aminoethoxy)-salicylamide required as starting material is obtained by catalytic debenzylation of 5-(2-benzylamino-ethoxy)-salicylamide by means of a 5% palladium-charcoal catalyst in methanol under normal conditions. After the hydrogen absorption is completed, the catalyst is filtered off, and the filtrate is concentrated under reduced pressure to thus obtain 5-(2-aminoethoxy)-salicylamide, m.p. 140°.

Sources & evidence

ORD record
ord-45597b0e86aa4a4ab3fd871dbd89a7f4
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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