4-Aminobenzonitrile → HCID 67526929, compound

HRID 133762Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:12]=[C:13]([NH:20][C:21]([C:23]2([CH3:26])[CH2:25][O:24]2)=[O:22])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18]>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][CH2:26][C:23]([OH:24])([CH3:25])[C:21]([NH:20][C:13]2[CH:14]=[CH:15][C:16]([N+:17]([O-:19])=[O:18])=[C:11]([CH3:10])[CH:12]=2)=[O:22])=[CH:3][CH:4]=1)#[N:7]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

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

Product 1

HCID 67526929HCID 67526929, compound

Procedure

3-(4-Cyanophenylamino)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide was prepared as described in Example 52 starting from 4-aminobenzonitrile and 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-5% methanol). 1H NMR (400 MHz, DMSO-d6): 1.41 (3H, s), 2.52 (3H, s), 3.25 (1H, dd, J=13.5 Hz, J=5.3 Hz), 3.52 (1H, dd, J=13.5 Hz, J=7.0 Hz), 6.08 (1H, s), 6.53 (1H, m), 6.75 (2H, d, J=8.8 Hz)), 7.39 (2H, d, J=8.8 Hz), 7.79-7.83 (2H, m), 8.01 (1H, d, J=8.9 Hz), 10.02 (1H, s).

Workup

customThe crude product was purified by flash chromatography (dichloromethane-5% methanol)

Sources & evidence

ORD record: ord-a3814bcc605a474baac6e0e3bfb9ff25
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390923B2

Reaction notes

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