Hydrazine hydrate (1:1) → HCID 13650167, compound

HRID 1981955Notes

Reaction equation

HRID 1981955 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([N+:18]([O-])=[O:19])[CH:15]=[CH:16][CH:17]=1.O.NN>O1CCCC1.[Pd]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([NH:18][OH:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 136311552-[(3-Nitrophenoxy)methyl]-1,3-benzothiazole

Product 1

HCID 13650167HCID 13650167, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(2-benzthiazolyl)methoxy]nitrobenzene (1.6 g), prepared as in Example 1B, in tetrahydrofuran with 10% palladium on carbon is slowly added hydrazine hydrate (0.4 ml). Fresh catalyst is added twice over 4 hours. The mixture is filtered through celite and the solvent is removed in vacuo to give 1.3 g (81% yield) of product, m.p. 112°-114° C.

Workup

  1. additionFresh catalyst is added twice over 4 hours
  2. filtrationThe mixture is filtered through celite
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d7dbf16cec4941dca4630df035e2e982
Source dataset
uspto-grants-1986_06
Patent number
US04594425

Reaction notes

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