Methylamine → 6-Bromo-N-methylquinoxalin-2-amine

HRID 1020739Notes

Reaction equation

HRID 1020739 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[N:5]2.[CH3:13][NH2:14]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:14][CH3:13])[CH:6]=[N:5]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 126864086-Bromo-2-chloroquinoxaline

Product 1

HCID 601459936-Bromo-N-methylquinoxalin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To solution of 6-bromo-2-chloro-quinoxaline (0.7 g, 1 eq, 2.87 mmol) in THF (6 mL) was added a solution of methyl amine in THF (3 mL) at room temperature. The mixture was stirred at room temperature for 2 h. After completion of the reaction, the volatiles were removed under vacuum and water (20 mL) was added to reaction mixture. The aqueous layer was extracted with ethyl acetate (15 mL×3). The organic layer was washed with water (20 mL) and brine (20 mL) and then dried over Na2SO4. The organic layer was concentrated under vacuum to afford the crude product.

Workup

  1. customAfter completion of the reaction
  2. customthe volatiles were removed under vacuum and water (20 mL)
  3. additionwas added to reaction mixture
  4. extractionThe aqueous layer was extracted with ethyl acetate (15 mL×3)
  5. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-56e1df7a9b4f44b58b10a8ddb77ea8c2
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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