Hydrazine hydrate (1:1) → HCID 86650747, compound

HRID 875212Notes

Reaction equation

HRID 875212 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)=[CH:5][N:4]=[CH:3]1.O.NN>O1CCCC1>[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)=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 74965495HCID 74965495, compound

Product 1

HCID 86650747HCID 86650747, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{6-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (1.87 g, 4.27 mmol) in tetrahydrofuran (20 mL) was added dropwise hydrazine hydrate (1.04 mL, 21.4 mmol). After stirring at room temperature for 29 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the filtrate concentrated in vacuo. Purification on silica gel afforded 6-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine [1.07 g, yield 77%; HPLC/MS: m/z=308 (M+H); log P(HCOOH)=0.29].

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification on silica gel

Sources & evidence

ORD record
ord-89da8211fc264d2ab502748b5a299fe4
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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