Hydrazine → HCID 135905331, compound

HRID 643393Notes

Reaction equation

HRID 643393 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)=[N:4][N:3]=1.NN>C(Cl)Cl.CCO>[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[N:3][N:4]=1

Participants

5

Reactant 2

HCID 9321Hydrazine2×HCID 136102517HCID 136102517, compound

Product 1

HCID 135905331HCID 135905331, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(3-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)methyl]-1H-isoindole-1,3(2H)-dione (2.00 g, 7.40 mmol) in DCM (10.0 mL) and EtOH (10.0 mL) was charged with hydrazine (0.58 mL, 18.5 mmol) and stirred at rt for 8 h, then heated to 45° C. for an additional 16 h. The reaction was charged with an additional 0.5 equiv of hydrazine (0.116 mL, 3.70 mmol) and heated to 45° C. for 4 h. The reaction mixture was allowed to cool to rt then filtered through a fritted funnel and the cake was washed with 2 portions of cold 1:1 EtOH/DCM (75 mL) and the filtrate was concentrated resulting in 622 mg of a pale yellow solid which was taken on to the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.21 (s, 3H), 3.72 (s, 2H); MS (ES+): m/z 141.06 [MH+].

Workup

  1. temperatureheated to 45° C. for an additional 16 h
  2. temperatureheated to 45° C. for 4 h
  3. temperatureto cool to rt
  4. filtrationthen filtered through a fritted funnel
  5. washthe cake was washed with 2 portions of cold 1:1 EtOH/DCM (75 mL)
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3ff5de195a2f4d0d827e20873e70384d
Source dataset
uspto-grants-2010_04
Patent number
US07700594B2

Reaction notes

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