Methylamine → 2-Chloro-4-(methylamino)-5-nitrobenzonitrile

HRID 1258700Notes

Reaction equation

HRID 1258700 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:11]=[C:10](F)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:5]=1[C:6]#[N:7]>C1COCC1>[Cl:3][C:4]1[CH:11]=[C:10]([NH:2][CH3:1])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 107267312-Chloro-4-fluoro-5-nitrobenzonitrile

Product 1

HCID 679576272-Chloro-4-(methylamino)-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of MeNH2 in THF (14.9 mL, 2 M, 29.8 mmol) was added dropwise to a solution of 2-chloro-4-fluoro-5-nitrobenzonitrile (3.0 g, 15 mmol) in THF (100 mL) at −20° C. The mixture was stirred at −20° C. for 1 h and thereafter concentrated, washed with brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting residue was washed with PE to give the sub-title compound.

Workup

  1. concentrationconcentrated
  2. washwashed with brine
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe resulting residue was washed with PE

Sources & evidence

ORD record
ord-f1119eec4ec94833850b30c3926a1f5a
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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