1-Fluoro-2-nitrobenzene → 4-Methyl-2-(2-nitro-phenylamino)-benzonitrile

HRID 131310

Reaction equation

HRID 131310 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].O.[OH-].[Li+]>CS(C)=O>[CH3:20][C:18]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([NH:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:19]=1

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 210935294-Methyl-2-(2-nitro-phenylamino)-benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 1-fluoro-2-nitro-benzene (5.34 g, 37.83 mmol), 2-amino-4-methyl-benzonitrile (5.00 g, 37.83 mmol), lithium hydroxide monohydrate (3.17 g, 75.66 mmol) and DMSO (70.0 ml) and stir at 55° C. Afer 16 hours; cool to ambient temperature, pour the mixture onto ice chips and stir. After 1 hour, remove the resulting yellow precipitate by vacuum filtration. Dry the precipitate under vacuum, recrystallize in ethanol to give 5.15 g (54%) of fine, amber colored needles: mp 162-164° C.; mass spectrum (ion spray): m/z 254.0 (M+1).

Workup

  1. customAfer 16 hours
  2. additionpour the mixture onto ice chips
  3. customremove the resulting yellow precipitate
  4. filtrationby vacuum filtration
  5. customDry the precipitate under vacuum
  6. customrecrystallize in ethanol
  7. customto give 5.15 g (54%) of fine, amber colored needles

Sources & evidence

ORD record
ord-357fcf9ce6314f65ad7576ea9c7b50b7
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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