Hydrazine hydrate (1:1) → HCID 178507469, compound

HRID 57273Notes

Reaction equation

HRID 57273 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[N:13][NH:12][C:11]=1[NH2:24].O.NN>C(O)C.[Ni]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2[C:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[C:11]([NH2:24])[NH:12][N:13]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178509111HCID 178509111, compound

Product 1

HCID 178507469HCID 178507469, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

An aqueous solution of Raney Ni (1 mL) was added to a suspension of 4-benzothiazol-2-yl-5-(4-nitrophenyl)-2H-pyrazol-3-ylamine (115 mg, 0.34 mmol) in ethanol (20 mL). To the vigorously stirring solution was added hydrazine hydrate dropwise in 3 portions (3×50 mg, 3 mmol in total), and the resulting mixture was then stirred for 2 hrs. The solids were removed by filtration and the mother liquor was evaporated to afford the crude material. The residue was purified by flash column chromatography eluting with CH2Cl2:MeOH=9:1 to yield 26 mg (25%) of the title compound as a cream coloured solid. MS (m/z, ES+): 308.1 (M+1, 100%).

Workup

  1. customThe solids were removed by filtration
  2. customthe mother liquor was evaporated
  3. customto afford the crude material
  4. customThe residue was purified by flash column chromatography
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-90abb46a760748a9be1be827199e3277
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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