Pyridine → Methyl 3-chloro-2-hydrazino7-methylquinoxaline-6-carboxylate

HRID 1189451Notes

Reaction equation

HRID 1189451 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:17])=[C:7]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[N:3]=1.N1C=CC=CC=1.O.[NH2:25][NH2:26]>CO>[Cl:12][C:11]1[C:2]([NH:25][NH2:26])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:6]([CH3:17])[CH:5]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24654Hydrazine hydrate (1:1)HCID 58575027Methyl 2,3-dichloro-7-methylquinoxaline-6-carboxylate

Product 1

HCID 86660662Methyl 3-chloro-2-hydrazino7-methylquinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3.57 g of methyl 2,3-dichloro-7-methylquinoxaline-6-carboxylate in 214 mL of methanol were added 7.0 mL of pyridine and 2.34 mL of hydrazine monohydrate at 0° C., and then the mixture was stirred at room temperature overnight. The mixture was concentrated until its total amount reached about 100 mL, and water was added thereto, followed by stirring at room temperature for 1 hour. The precipitate was collected by filtration, washed with water and ethanol, and dried under reduced pressure to obtain 2.94 g of methyl 3-chloro-2-hydrazino-7-methylquinoxaline-6-carboxylate.

Workup

  1. concentrationThe mixture was concentrated until its total amount
  2. additionwas added
  3. stirringby stirring at room temperature for 1 hour
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water and ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc8a12b1029845ad90b00d99059219ba
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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