Hydrazine hydrate (1:1) → HCID 54554464, compound

HRID 343798Notes

Reaction equation

HRID 343798 reaction equation
O.NN.[Cl:4][C:5]1[C:6]([N:20]([CH2:25][CH2:26][N:27]2C(=O)C3=CC=CC=C3C2=O)[S:21]([CH3:24])(=[O:23])=[O:22])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11]=[C:10]([O:16][CH3:17])[C:9]([O:18][CH3:19])=[N:8]2>ClCCl.CO>[Cl:4][C:5]1[C:6]([N:20]([CH2:25][CH2:26][NH2:27])[S:21]([CH3:24])(=[O:23])=[O:22])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11]=[C:10]([O:16][CH3:17])[C:9]([O:18][CH3:19])=[N:8]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53817008HCID 53817008, compound

Product 1

HCID 54554464HCID 54554464, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Hydrazine hydrate (696 μl, 716 mg, 14.3 mmol) was added dropwise to a solution of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-phthalimidoethyl)methanesulphonamide (3.76 g, 7.15 mmol) in a mixture of dichloromethane (71 ml) and methanol (5 ml) at room temperature under nitrogen. The mixture was heated at reflux for 4 days and then further methanol (20 ml) was added. After a further 2 days the mixture was allowed to cool and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and this was extracted 3 times with 10% aqueous citric acid. The combined acid extracts were adjusted to pH 9 with solid potassium carbonate and extracted 3 times with dichloromethane. The combined dichloromethane extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 95:5 dichloromethane:methanol to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-aminoethyl)methanesulphonamide (1.96 g, 69%) as a pale yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 days
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionthis was extracted 3 times with 10% aqueous citric acid
  7. extractionextracted 3 times with dichloromethane
  8. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel eluting with 95:5 dichloromethane

Sources & evidence

ORD record
ord-63296f7fe705488e848402049d477ed5
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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