Hydrazine hydrate (1:1) → HCID 57470539, compound

HRID 1270158Notes

Reaction equation

HRID 1270158 reaction equation
O.[NH2:2][NH2:3].[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13](Cl)[C:12]([Cl:19])=[N:11]2)=[O:7]>CO>[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([NH:2][NH2:3])[C:12]([Cl:19])=[N:11]2)=[O:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 13799594Methyl 2,3-dichloroquinoxaline-6-carboxylate

Product 1

HCID 57470539HCID 57470539, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Hydrazine monohydrate (0.26 mL) was added dropwise to a suspension of 2,3-dichloro-quinoxaline-6-carboxylic acid methyl ester (1.2 g) in methanol (10 mL) at −10° C. After three hrs. at this temperature, an additional portion of hydrazine monohydrate (0.26 mL) was added, and the resulting mixture was stirred at 0° C. for three hrs., and then for one hr. at 23° C. The suspension was filtered, and the solids were washed with MeOH. Flash column chromatography provided a residue that was recrystallized from MeOH to provide 3-chloro-2-hydrazino-quinoxaline-6-carboxylic acid methyl ester as a yellow solid. MS (M+H)+=253.2.

Workup

  1. wait, and then for one hr
  2. customat 23° C
  3. filtrationThe suspension was filtered
  4. washthe solids were washed with MeOH
  5. customFlash column chromatography provided a residue that
  6. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-aa2499738a664bf9816f1d4e2875dc1a
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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