N-methyl-2-pyrrolidone → HCID 19851163, compound

HRID 1606850Notes

Reaction equation

HRID 1606850 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([NH2:9])[C:3]=1[N+:10]([O-:12])=[O:11].CN1CCC[C:15]1=[O:19]>C[O-].[Na+].CO>[NH2:1][C:2]1[CH:7]=[C:6]([O:19][CH3:15])[CH:5]=[C:4]([NH2:9])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 20071078HCID 20071078, compound

Product 1

HCID 19851163HCID 19851163, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

0.024 mole (4.5 g) of 2,6-diamino-4-chloronitrobenzene in 9 ml of N-methylpyrrolidone and 22.5 ml of 30% sodium methylate in methanol were refluxed for 4 hours 30 minutes. Upon dilution of the reaction medium with water, the desired product precipitated out. After filtering, water washing and vacuum drying in the presence of P2O5, the product obtained was recrystallized from toluene; a black insoluble product was eliminated by hot filtration. The desired product melted at 140° C.

Workup

  1. customUpon dilution of the reaction medium with water, the desired product precipitated out
  2. filtrationAfter filtering
  3. dry with materialwater washing and vacuum drying in the presence of P2O5
  4. customthe product obtained
  5. customwas recrystallized from toluene
  6. filtrationa black insoluble product was eliminated by hot filtration

Sources & evidence

ORD record
ord-7f25a4c70d0e4104b5d01a9b0c606f95
Source dataset
uspto-grants-1989_09
Patent number
US04863482

Reaction notes

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