Potassium Carbonate → HCID 67916519, compound

HRID 1030272Notes

Reaction equation

HRID 1030272 reaction equation
CNC[C:4]1[CH:13]=[N:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:14](=[O:17])([O-])[O-].[K+].[K+].ICCC[C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[O:33][C:34]1C=CC([N+]([O-])=O)=[CH:36][C:35]=1CCCI.[C:47](#[N:49])C.C(O)C>>[N+:30]([C:28]1[CH:29]=[CH:24][C:25]([O:33][CH2:34][CH2:35][CH2:36][O:17][CH2:14][NH:49][CH2:47][N:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH2:13]2)=[CH:26][CH:27]=1)([O-:32])=[O:31]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 15675889N-Methyl-1-(quinoxalin-2-yl)methanamineHCID 21984225Acetonitrile ethanolHCID 86745674HCID 86745674, compound

Product 1

HCID 67916519HCID 67916519, compoundYield 83%

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 2-(methylaminomethyl)quinoxaline (1.10 g, 6.35 mmol) and potassium carbonate (0.88 g, 6.35 mmol) in 2:1 acetonitrile/ethanol (40 mL) was added 3-iodopropyl-4-nitrophenyl ether (1.95 g, 6.35 mmol). The resulting mixture was heated at 85° C. overnight, concentrated, and partitioned between ethyl acetate and 10% aqueous potassium carbonate. The organic phase was dried (MgSO4), decolorized (charcoal), and concentrated to afford 1.86 g (83%) of product as a yellow semi-solid which was of sufficient purity to use in the next step.

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and 10% aqueous potassium carbonate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9e4beb06eca54ae39518f03e3145916f
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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