3-tert-Butylaniline → (3-tert-Butyl-phenyl)-(6-methoxy-quinoxalin-2-yl)-amine

HRID 639364Notes

Reaction equation

HRID 639364 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[C:14]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])([CH3:17])([CH3:16])[CH3:15]>C(O)C>[C:14]([C:18]1[CH:19]=[C:20]([NH:21][C:2]2[CH:11]=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[N:3]=2)[CH:22]=[CH:23][CH:24]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 793343-tert-ButylanilineHCID 126864122-Chloro-6-methoxyquinoxaline

Product 1

HCID 59254854(3-tert-Butyl-phenyl)-(6-methoxy-quinoxalin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution containing 2-chloro-6-methoxyquinoxaline (synthesized as described in J. Chem. Soc. Perkin Trans 2001, 978-984) (1 eq), 3-t-butylaniline (2 eq) in ethanol was heated at 80° C. overnight. The resultant mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried. Purification on silica gel gave the desired product.

Workup

  1. concentrationThe resultant mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-34312f49209e437da91e98621bf16cd9
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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