1-Fluoro-2-nitrobenzene → 5-Methyl-2-(2-nitro-phenylamino)-benzonitrile

HRID 131311

Reaction equation

HRID 131311 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]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=1[C:14]#[N:15].O.[OH-].[Li+]>CS(C)=O>[CH3:20][C:17]1[CH:18]=[CH:19][C:12]([NH:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[C:13]([CH:16]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 2427782-Amino-5-methylbenzonitrile

Product 1

HCID 210935375-Methyl-2-(2-nitro-phenylamino)-benzonitrileYield 57.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

Combine 1-fluoro-2-nitro-benzene (4.34 g, 30.79 mmol), 2-amino-5-methyl-benzonitrile (4.07 g, 30.79 mmol), lithium hydroxide monohydrate (2.58 g, 61.58 mmol) and DMSO (50.0 ml). Stir the mixture at 55° C. for 22 hours, cool to ambient temperature and pour the mixture onto ice chips and stir. After 1 hour, remove the resulting precipitate by vacuum filtration. Dry the precipitate under vacuum, purify on silica gel using dichloromethane/hexanes (75:25) to give 4.45 g (57%) of an orange solid: mp 135-139° C.; mass spectrum (ion spray): m/z=254.0 (M+1).

Workup

  1. temperaturecool to ambient temperature
  2. additionpour the mixture onto ice chips
  3. stirringstir
  4. waitAfter 1 hour
  5. customremove the resulting precipitate
  6. filtrationby vacuum filtration
  7. customDry the precipitate under vacuum
  8. custompurify on silica gel

Sources & evidence

ORD record
ord-59a7b2194a9e4d2abdfafb97986af174
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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