Methacryloyl chloride → N-[3-(Hydroxymethyl)-4-nitrophenyl]-2-methylprop-2-enamide

HRID 133758Notes

Reaction equation

HRID 133758 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.[C:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15]>>[OH:9][CH2:8][C:6]1[CH:7]=[C:2]([NH:1][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 13528Methacryloyl chlorideHCID 13238551(5-Amino-2-nitrophenyl)methanol

Product 1

HCID 67527004N-[3-(Hydroxymethyl)-4-nitrophenyl]-2-methylprop-2-enamide

Procedure

N-(3-Hydroxymethyl-4-nitrophenyl)-2-methylacrylamide was prepared as described in Example 1a starting from (5-Amino-2-nitrophenyl)methanol and methacryloyl chloride. 1H NMR (400 MHz, DMSO-d6): 1.97 (3H, s), 4.85 (2H, d, J=5.2 Hz), 5.56 (1H, t, J=5.2 Hz), 5.61 (1H, s), 5.90 (1H, s), 7.93 (1H, dd, J=9.0 Hz, J=2.1 Hz), 8.11 (1H, d, J=9.0 Hz), 8.20 (1H, d, J=2.1 Hz), 10.32 (1H, s).

Sources & evidence

ORD record
ord-8fbfa66a81f142b6bd437f6f3357c304
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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