Methylhydrazine → HCID 10444799, compound

HRID 1646216Notes

Reaction equation

HRID 1646216 reaction equation
C[N:2]([CH:4]=[C:5]1[CH2:18][CH2:17][C:16]2[C:7](=[C:8]([N:19]=CN(C)C)[C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]1=O)C.[CH3:25][NH:26]N>CCO>[NH2:19][C:8]1[C:9]2[C:14]([N:15]=[C:16]3[C:7]=1[C:6]1[N:26]([CH3:25])[N:2]=[CH:4][C:5]=1[CH2:18][CH2:17]3)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 54137271HCID 54137271, compound

Product 1

HCID 10444799HCID 10444799, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dihydro-2-[(dimethylamino)methylene]-9-[[(dimethylamino)methylene]amino]acridin-1-(2H)-one (3.0 g) was refluxed for 60 min in 150 mL of EtOH containing 8.0 g of methylhydrazine. At the end of this time the solvent was evaporated under reduced pressure and then the residue was adhered to silica with MeOH. Purification by flash chromatography (toluene:MeOH:Et3N, 19:1:1) gave 1.71 g of material which was pure to TLC. This was combined with the product of another run of smaller size and recrystallized from toluene to give analytically pure product, mp 240° (d).

Workup

  1. customAt the end of this time the solvent was evaporated under reduced pressure
  2. customPurification by flash chromatography (toluene:MeOH:Et3N, 19:1:1)

Sources & evidence

ORD record
ord-48089f648422491e87706131cae97cf5
Source dataset
uspto-grants-1993_01
Patent number
US05179100

Reaction notes

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