2-Aminophenol → N-(2-Hydroxyphenyl)prop-2-enamide

HRID 547240Notes

Reaction equation

HRID 547240 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9](Cl)(=[O:12])[CH:10]=[CH2:11].[Cl-].[Li+]>CN1CCCC1=O>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:9](=[O:12])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 13140Acryloyl chlorideHCID 433294Lithium Chloride

Product 1

HCID 12998435N-(2-Hydroxyphenyl)prop-2-enamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Among the (meth)acrylamide derivatives represented by the general formula (1), a compound (the above compound A-1) in which R1 is a hydrogen atom; R2 is an ethoxymethyl group; and R3 to R6 are a hydrogen atom can be synthesized, for example, by the following manner. In this manner, o-aminophenol is reacted with acryloyl chloride in N-methyl-2-pyrrolidone (NMP) in the presence of lithium chloride to obtain N-(2-hydroxyphenyl)acrylamide. N-(2-hydroxyphenyl)acrylamide is then reacted with chloromethyl ethyl ether in NMP in the presence of N,N-diisopropyl ethylamine to synthesize the above compound A-1.

Sources & evidence

ORD record
ord-d4e903e85a594f5b8fefebb323e0f11b
Source dataset
uspto-grants-2011_05
Patent number
US07939241B2

Reaction notes

Loading…