3-Fluoro-4-nitrophenol → 3-(3-Fluoro-4-nitrophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

HRID 133741

Reaction equation

HRID 133741 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][C:13]1[CH:14]=[C:15]([NH:22][C:23]([C:25]2([CH3:28])[CH2:27][O:26]2)=[O:24])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH2:28][C:25]([OH:26])([CH3:27])[C:23]([NH:22][C:15]1[CH:16]=[CH:17][C:18]([N+:19]([O-:21])=[O:20])=[C:13]([CH3:12])[CH:14]=1)=[O:24]

Participants

3

Reactant 2

HCID 5209483-Fluoro-4-nitrophenolHCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Product 1

HCID 866127373-(3-Fluoro-4-nitrophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Procedure

3-(3-Fluoro-4-nitrophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide was prepared as described in Example 1 starting from 3-fluoro-4-nitrophenol and 2-methyl-oxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide. 1H NMR (DMSO-d6): 1.46 (3H, s), 2.53 (3H, s), 4.16 (1H, d, J=10.1 Hz), 4.41 (1H, d, J=10.1 Hz), 6.36 (1H, bs), 6.96 (1H, m), 7.22 (1H, m), 7.88 (1H, dd, J=9.0 Hz and 2.1 Hz), 7.90 (1H, d, J=2.1 Hz), 8.04 (1H, d, J=9.0 Hz), 8.24 (1H, m), 10.19 (1H, s).

Sources & evidence

ORD record
ord-b2c24e9b39cf42d3ae77ca7650bfcffd
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Linked notes

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