Stannous chloride dihydrate → 6-Chloro-3-methylquinoxalin-5-amine

HRID 1968747Notes

Reaction equation

HRID 1968747 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[C:16]([N+:17]([O-])=O)=[C:15]2[C:10]([N:11]=[CH:12][C:13]([CH3:20])=[N:14]2)=[CH:9][CH:8]=1>CCOC(C)=O.C(O)C>[Cl:6][C:7]1[C:16]([NH2:17])=[C:15]2[C:10](=[CH:9][CH:8]=1)[N:11]=[CH:12][C:13]([CH3:20])=[N:14]2

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 668825737-Chloro-2-methyl-8-nitro-quinoxaline

Product 1

HCID 668833186-Chloro-3-methylquinoxalin-5-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tin(II)-chloride dihydrate (21.7 g, 96.12 mmol, 5.4 equiv) was added at room temperature to a solution of 7-chloro-2-methyl-8-nitro-quinoxaline (3.98 g, 17.80 mmol) in a mixture of EtOAc (56 ml) and ethanol (28 ml). After 40 minutes at 80° C., the reaction mixture was cooled to room temperature, diluted with ice water, filtered, and extracted with EtOAc. The combined organic layers were washed with concentrated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford 6-chloro-3-methyl-quinoxalin-5-ylamine, which was used in the next transformation without purification. MS (ES+): 194.2 (M+H)+.

Workup

  1. filtrationfiltered
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with concentrated aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a04c5e42ec064b4fab196b4a65c5b175
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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