2-Methyl-4-nitroaniline → 2-Methyl-N-(2-methyl-4-nitrophenyl)acrylamide

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12](Cl)(=[O:16])[C:13]([CH3:15])=[CH2:14]>>[CH3:15][C:13](=[CH2:14])[C:12]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[CH3:1])=[O:16]

Participants

Reactant 2

HCID 74412-Methyl-4-nitroaniline

HCID 13528Methacryloyl chloride

Product 1

HCID 450976412-Methyl-N-(2-methyl-4-nitrophenyl)acrylamide

Procedure

2-Methyl-N-(2-methyl-4-nitrophenyl)acrylamide was prepared as described in Example 1a starting from 2-methyl-4-nitroaniline and methacryloyl chloride. 1H NMR (400 MHz, DMSO-d6): 1.98 (3H, s), 2.34 (3H, s), 5.59 (1H, s), 5.91 (1H, s), 7.74 (1H, d, J=8.8 Hz), 8.07 (1H, dd, J=8.8 Hz, J=2.7 Hz), 8.15 (1H, d, J=2.6 Hz), 9.53 (1H, s).

Sources & evidence

ORD record: ord-6429a302fea4436291a646d47d1a4a68
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390923B2

Reaction notes

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