Hydrazine hydrate (1:1) → HCID 10199026, compound

HRID 1825725Notes

Reaction equation

HRID 1825725 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]2[NH:8][C:9](=[O:18])/[C:10](=[CH:12]/[C:13]3[NH:14][CH:15]=[CH:16][CH:17]=3)/[S:11][C:6]=2[CH:5]=1)([O-])=O.O.NN>[Ni].C(O)C>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]2[NH:8][C:9](=[O:18])/[C:10](=[CH:12]/[C:13]3[NH:14][CH:15]=[CH:16][CH:17]=3)/[S:11][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9882369HCID 9882369, compound

Product 1

HCID 10199026HCID 10199026, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A catalytic amount of Raney nickel was added portionwise with stirring to a mixture of (Z)-7-nitro-2-[(pyrrol-2-yl)methylene]-2H-1,4-benzothiazin-3(4H)-one (Example 5) (0.43 g, 1.5 mmol) and hydrazine hydrate (98%) (0.8 ml) in ethanol (20 ml). The reaction mixture heated under reflux for 5.5 hours, then filtered and the solvent removed in vacuo. The product was purified by silica gel chromatography using a gradient of (98:2) to (95:5) toluene:ethanol as the mobile phase.

Workup

  1. temperatureThe reaction mixture heated
  2. temperatureunder reflux for 5.5 hours
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2720684e7f904edc8fce5df3b0d1b564
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

Loading…