Water → 6-Chloro-2-(methylamino)-3-nitrobenzonitrile

HRID 1760749Notes

Reaction equation

HRID 1760749 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5].[CH3:14][NH2:15].O.CCCCCC>CCOC(C)=O>[Cl:13][C:6]1[C:3]([C:4]#[N:5])=[C:2]([NH:15][CH3:14])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329Methylamine2×HCID 8058HexaneHCID 44619322,6-Dichloro-3-nitrobenzonitrile

Product 1

HCID 112180896-Chloro-2-(methylamino)-3-nitrobenzonitrileYield 83.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,6-dichloro-3-nitrobenzonitrile (98.7 g, 0.455 mol) in EtOAc (910 mL) was cooled to 5° C. 40% Aqueous methylamine (79.5 mL, 1.14 mol) was added with vigorous mechanical stirring, keeping the temperature at 10-15° C. After addition was complete, stirring was continued for 3 h at the same temperature. More methylamine (16 mL, 0.23 mol) was added, and the mixture stirred for a further 1.5 h at room temperature. Water (300 mL) was added, followed by hexane (450 mL). The mixture was stirred for 15 min, filtered, and the solid washed with water and MeOH, to give 6-chloro-2-methylamino-3-nitrobenzonitrile (80.3 g, 83%), mp 167-170° C.

Workup

  1. customat 10-15° C
  2. additionAfter addition
  3. stirringthe mixture stirred for a further 1.5 h at room temperature
  4. stirringThe mixture was stirred for 15 min
  5. filtrationfiltered
  6. washthe solid washed with water and MeOH

Sources & evidence

ORD record
ord-9cd88a867a6d421b97d2646b432607a5
Source dataset
uspto-grants-2005_01
Patent number
US06844435B2

Reaction notes

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