Methylhydrazine → HCID 53403401, compound

HRID 1498921Notes

Reaction equation

HRID 1498921 reaction equation
[CH3:1][NH:2][NH2:3].[CH3:4][O:5][C:6]1[CH:25]=[CH:24][C:9](CCNN2C(=O)C3C(=CC=CC=3)C2=O)=[CH:8][C:7]=1[CH3:26].O1CCC[CH2:28]1>>[CH3:4][O:5][C:6]1[CH:25]=[CH:24][C:9]([CH2:1][N:2]([CH3:28])[NH2:3])=[CH:8][C:7]=1[CH3:26]

Participants

4

Reactant 3

HCID 6061Methylhydrazine2×HCID 8028TetrahydrofuranHCID 86679345HCID 86679345, compound

Product 1

HCID 53403401HCID 53403401, compoundYield 31%

Procedure

Tetrahydrofuran (30 ml) and methylhydrazine (138 mg) were added to 2-[(4-methoxy-3-methylbenzyl)methylamino]isoindole-1,3-dione (621 mg) prepared in the Step 15-1-3, and the mixture was stirred at a room temperature for one hour. Another methylhydrazine (138 mg) was added thereto, the resulting mixture was stirred for 12 hours. The solvent was distilled off under a reduced pressure. Dichloromethane was added to the residue, and the insoluble matter was removed by filtration. The filtrate was concentrated under a reduced pressure and then purified by silica gel column chromatography (dichloromethane:methanol=20:1) to give the title compound (115 mg, 31%).

Workup

  1. customprepared in the Step 15-1-3
  2. stirringthe resulting mixture was stirred for 12 hours
  3. distillationThe solvent was distilled off under a reduced pressure
  4. additionDichloromethane was added to the residue
  5. customthe insoluble matter was removed by filtration
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. custompurified by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-a840e156235c4e48ab86a9d44e9258d5
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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