Hydrazine hydrate (1:1) → 3-(1,3-Thiazol-2-yl)aniline

HRID 2262749Notes

Reaction equation

HRID 2262749 reaction equation
Cl[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:4][CH:3]=1.O.NN>C1COCC1.[Ni]>[S:6]1[CH:2]=[CH:3][N:4]=[C:5]1[C:7]1[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 575722385-Chloro-2-(3-nitro-phenyl)-thiazole

Product 1

HCID 110193903-(1,3-Thiazol-2-yl)anilineYield 86.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-2-(3-nitro-phenyl)-thiazole (20.0 g, 69.6 mmol) in THF (260 ml) was added hydrazine monohydrate (13.5 ml, 278 mmol) and Raney nickel (2 g). The resultant mixture was stirred at ambient conditions for 1 hour and then filtered through celite. The filtrate was evaporated to dryness and the filtrate was partitioned between ethyl acetate and saturated, aqueous sodium carbonate. The organic layer was dried over sodium sulphate and concentrated in vacuo. The concentrate was eluted through silica gel with a mixture of ethyl acetate and ligroin (1:3 v/v) to afford the desired product (10.6 g, 72%).

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate was evaporated to dryness
  3. customthe filtrate was partitioned between ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. washThe concentrate was eluted through silica gel with a mixture of ethyl acetate and ligroin (1:3 v/v)

Sources & evidence

ORD record
ord-245ad76fcb924d85a64583802b27a633
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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