Hydrazine hydrate (1:1) → HCID 86653133, compound

HRID 1258577Notes

Reaction equation

HRID 1258577 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([CH2:23][N:24]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][N: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]([CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86653134HCID 86653134, compound

Product 1

HCID 86653133HCID 86653133, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-({6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methyl)-1H-isoindole-1,3(2H)-dione (3 g, 6.61 mmol, 1 eq.) in 25 ml of THF was added hydrazine hydrate (1.32 g, 26.46 mmol, 4 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 1-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methanamine (2.29 g, 93%) 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-d6a7f6ffd54d456d8f48332beb3b5e42
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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