Methacryloyl chloride → N-(3-Ethyl-4-nitrophenyl)-2-methylprop-2-enamide

HRID 133780Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([NH2:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[CH3:2].[C:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15]>>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:12][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[CH3:2]

Participants

Reactant 2

HCID 13528Methacryloyl chloride

HCID 22708665HCID 22708665, compound

Product 1

HCID 67526083N-(3-Ethyl-4-nitrophenyl)-2-methylprop-2-enamide

Procedure

N-(3-Ethyl-4-nitrophenyl)-2-methylacrylamide was prepared as described in Example 1a starting from 3-ethyl-4-nitrophenylamine (W. Pfleiderer et al. U.S. 2002/0146737 A1) and methacryloyl chloride. The crude product was purified by flash chromatography using heptane/ethyl acetate (9:1) as an eluent. 1H NMR (400 MHz, DMSO-d6): 1.22 (3H, t, 3J=7.4 Hz), 1.97 (3H, s), 2.87 (2H, q, 3J=7.4 Hz), 5.62 (1H, s), 5.88 (1H, s), 7.81 (1H, dd, 3J=8.9 Hz, 4J=2.3 Hz), 7.83 (1H, d, 4J=2.2 Hz), 8.00 (1H, d, 3J=8.8 Hz), 10.21 (1H, s, —NHCO—).

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-b4acaefce82b492c8703d8b638cf89e4
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390923B2

Reaction notes

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