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

HRID 407332Notes

Reaction equation

HRID 407332 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-ce597fa1d7cf40b0a895c5c9d0bf0ad6
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

Loading…