Dimethylformamide → 2(1H)-Quinoxalinone, 3,4-dihydro-

HRID 717764

Reaction equation

HRID 717764 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(N([CH2:14][CH3:15])CC)C.CN(C=[O:20])C>>[NH:7]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:8][CH2:15][C:14]1=[O:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 8471Triethylamine

Product 1

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-

Conditions

Temperature
80 °C

Procedure

To a solution of o-phenylenediamine (4 g, 37.03 mmol) in DMF (30 mL) was added triethylamine (10.3 mL, 74.06) followed by ethyl-2-bromo acetate (4.53 mL, 40.73 mmol). The reaction was stirred at RT for 16 h and at 80° C. for 3 h. The reaction was monitored by TLC. After completion of reaction, the DMF was removed under vacuum. Water (20 mL) was added to the reaction mixture, which was then extracted with EtOAc (300 mL). The organic layer was dried over sodium sulfate, concentrated under vacuum, and the product recrystallized with DCM/hexane in 1:1 ratio to obtain 2.2 g of desired compound.

Workup

  1. customAfter completion of reaction
  2. customthe DMF was removed under vacuum
  3. additionWater (20 mL) was added to the reaction mixture, which
  4. extractionwas then extracted with EtOAc (300 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customthe product recrystallized with DCM/hexane in 1:1 ratio

Sources & evidence

ORD record
ord-6021c58e75c1457b949ae4f6c2098976
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Linked notes

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