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

HRID 1350503Notes

Reaction equation

HRID 1350503 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

Conditions

Temperature
55 °C

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). Stir the mixture at 55° C. for 16 hours then cool it to ambient temperature. Pour the mixture onto ice chips and stir for 1 hour. Remove the resulting yellow precipitate by vacuum filtration. Dry the precipitate under vacuum then recrystallize it in ethanol to give 5.15 g (54%) of fine, amber colored needles: mp 162–164°; mass spectrum (ion spray): m/z=254.0 (M+1).

Workup

  1. temperaturethen cool it to ambient temperature
  2. additionPour the mixture onto ice chips
  3. stirringstir for 1 hour
  4. customRemove the resulting yellow precipitate
  5. filtrationby vacuum filtration
  6. customDry the precipitate under vacuum
  7. customthen recrystallize it in ethanol
  8. customto give 5.15 g (54%) of fine, amber colored needles

Sources & evidence

ORD record
ord-b8f1c9b8df5b401d9c01e94183af269a
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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