Hydrazine hydrate (1:1) → HCID 86650766, compound

HRID 875237Notes

Reaction equation

HRID 875237 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([N:23]3C(=O)C4C(=CC=CC=4)C3=O)[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][CH:4]=[N:3]1.O.NN>C1COCC1>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86650765HCID 86650765, compound

Product 1

HCID 86650766HCID 86650766, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{6-[({[(1-methyl-1H-1,2,4-triazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (11.27 g, 25.70 mmol, 1 eq.) in 500 ml of THF was added hydrazine hydrate (6.43 g, 128.52 mmol, 5 eq.). The reaction was stirred overnight at room temperature. The solvent was evaporated and the residue dissolved in EtOAc. Water was added and the layers separated. The aqueous layer was extracted with EtOAc and the organics were combined, dried over MgSO4 and concentrated to give 6-[({[(1-methyl-1H-1,2,4-triazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (7.85 g, 99%) as a clear viscous oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. additionWater was added
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b0909987ebf44addb3c9fb17b39880cf
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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