Dihydrocoumarin → N,N-diethyl-3-(2-hydroxyphenyl)propanamide

HRID 2184641

Reaction equation

HRID 2184641 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH:6]1[CH:7]=[CH:8][C:9]2[O:16][C:14](=[O:15])[CH2:13][CH2:12][C:10]=2[CH:11]=1>>[CH2:1]([N:3]([CH2:4][CH3:5])[C:14](=[O:15])[CH2:13][CH2:12][C:10]1[CH:11]=[CH:6][CH:7]=[CH:8][C:9]=1[OH:16])[CH3:2]

Participants

3

Reactant 2

HCID 660DihydrocoumarinHCID 8021Diethylamine

Product 1

HCID 45803915N,N-diethyl-3-(2-hydroxyphenyl)propanamideYield 113.8%

Procedure

Diethylamine (98.5 g) and dihydrocoumarin (20.0 g) were refluxed for 4 hours. Excess diethylamine was removed in vacuo to leave 34.0 g of N,N-diethyl-3-(2-hydroxyphenyl) propionamide. 1H NMR (CDCl3): 7.26-7.03 (m, 2H), 6.91 (dd, 1H), 6.81 (td, 1H), 3.37 (quartet, 2H), 3.26 (quartet, 2H), 2.95 (m, 2H), 2.71 (m, 2H), 1.10 (quartet, 6H).

Workup

  1. customExcess diethylamine was removed in vacuo

Sources & evidence

ORD record
ord-fa0321f61cef42a89d0c6a5c6af1d9ab
Source dataset
uspto-grants-2002_06
Patent number
US06399534B2

Linked notes

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