Hydrazine hydrate (1:1) → HCID 59818282, compound

HRID 244591Notes

Reaction equation

HRID 244591 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:15][N:16]=1.O.NN>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:15][N:16]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59818280HCID 59818280, compound

Product 1

HCID 59818282HCID 59818282, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (2-methyl-5-nitro-phenyl)-(5-pyridin-4-yl-oxazol-2-yl)-amine (1 g, 3.39 mmol) in ethanol (50 mL) was treated with 10% Pd/C (120 mg) and hydrazine hydrate (3.50 mL, 112.5 mmol) was added drop wise over 10 min. The reaction mixture was stirred at room temperature for 30 min and then refluxed for 2 h. The hot solution was filtered through a short pad of Celite, and the catalyst was washed with hot ethanol. The filtrates were concentrated under reduced vacuum to give the crude product. This was silica gel column chromatographed (dichloromethane/ethanol: 97/3). 720 mg (80%) of (2-methyl-5-amino-phenyl)-(5-pyridin-4-yl-oxazol-2-yl)-amine was obtained as pale yellow powder.

Workup

  1. additionwas added drop wise over 10 min
  2. temperaturerefluxed for 2 h
  3. filtrationThe hot solution was filtered through a short pad of Celite
  4. washthe catalyst was washed with hot ethanol
  5. concentrationThe filtrates were concentrated under reduced vacuum
  6. customto give the crude product
  7. customThis was silica gel column chromatographed (dichloromethane/ethanol: 97/3)

Sources & evidence

ORD record
ord-7aa9a73d10944a129d0e71c74b8f5b4f
Source dataset
uspto-grants-2014_02
Patent number
US08658659B2

Reaction notes

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