Hydrazine hydrate (1:1) → 6-[({[(4-Methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

HRID 875190Notes

Reaction equation

HRID 875190 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](=[N:14][O:15][CH2:16][C:17]1[N:22]=[C:21]([N:23]2C(=O)C3C(=CC=CC=3)C2=O)[CH:20]=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.NN>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](=[N:14][O:15][CH2:16][C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866507302-{6-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 866507316-[({[(4-Methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amineYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{6-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (0.3 g, 0.69 mmol) dissolved in tetrahydrofuran (7 mL) was added hydrazine hydrate (171 mg, 3.4 mmol). After stirring for 24 hours at room temperature the precipitate formed was filtered. The filtrate was evaporated and purified on silica affording 6-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (0.19 g, 85%).

Workup

  1. customformed
  2. filtrationwas filtered
  3. customThe filtrate was evaporated
  4. custompurified on silica

Sources & evidence

ORD record
ord-80157e79e65c4db4b52cb5aade40d441
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

Loading…