4-Methoxy cinnamic acid → 3-(4-Methoxy-phenyl)-N-(3-methyl-1-propyl-butyl)-acrylamide

HRID 339368Notes

Reaction equation

HRID 339368 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.[CH3:14][CH:15]([CH3:22])[CH2:16][CH:17]([NH2:21])[CH2:18][CH2:19][CH3:20]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH:10][C:11]([NH:21][CH:17]([CH2:18][CH2:19][CH3:20])[CH2:16][CH:15]([CH3:22])[CH3:14])=[O:13])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 132454-Methoxy cinnamic acidHCID 144181752-Methylheptan-4-amine

Product 1

HCID 667733783-(4-Methoxy-phenyl)-N-(3-methyl-1-propyl-butyl)-acrylamideYield 65%

Procedure

Prepared in a similar manner to example 4 using 3-(4-methoxy-phenyl)-acrylic acid and 3-methyl-1-propyl-butylamine (example 2a). Yield: 65%. 1H NMR (500 MHz, CDCl3): δ 0.90-0.95 (m, 9H), 1.30-1.39 (m, 5H), 1.49-1.50 (m, 1H), 1.64-1.67 (m, 1H), 3.82 (s, 3H), 4.17-4.18 (m, 1H), 5.18-5.20 (d, 1H), 6.22-6.26 (d, 1H), 6.86-6.89 (d, 2H), 7.42-7.45 (d, 2H), 7.56-7.59 (d, 1H). MS (M+H, 290.1).

Sources & evidence

ORD record
ord-48e0007f343348499a33f92685dceb29
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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