Hydrazine hydrate (1:1) → HCID 57250218, compound

HRID 1825730Notes

Reaction equation

HRID 1825730 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]2[NH:8][C:9](=[O:22])[C:10](=[CH:12][C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)[S:11][C:6]=2[CH:5]=1)([O-])=O.O.NN>[Ni].C(O)C>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]2[NH:8][C:9](=[O:22])[C:10](=[CH:12][C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)[S:11][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57185708HCID 57185708, compound

Product 1

HCID 57250218HCID 57250218, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A catalytic amount of Raney nickel was added portionwise with stirring to a mixture of 7-nitro-2-[(indol-3-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one (see Example 31) (0.39 g, 1.16 mmol) and hydrazine hydrate (98%) (0.60 ml) in ethanol (15 ml). The reaction mixture was refluxed for 5 h, then filtered hot. The solid residue was boiled with ethanol (100 ml) and filtered hot. The combined filtrates were brought to dryness in vacuo and chromatographed on silica gel using a gradient of (9:1) to (8:2) dichloromethane:ethanol as the mobile phase to afford 0.17 g (35%) product.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. filtrationfiltered hot
  3. filtrationfiltered hot
  4. customchromatographed on silica gel using a gradient of (9:1) to (8:2) dichloromethane

Sources & evidence

ORD record
ord-b9451cde7532414ca9d0ec269e438c1d
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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