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

HRID 1771969Notes

Reaction equation

HRID 1771969 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9][C:8]1=O>C1COCC1>[NH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-HCID 21226445Aluminium lithium hydride

Product 1

HCID 770281,2,3,4-TetrahydroquinoxalineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminum hydride (28.2 g, 742 mmol) in THF (1500 mL) at 0° C. was added 3,4-dihydroquinoxalin-2(1H)-one (50 g, 337 mmol) portion wise. The reaction mixture was warmed up to room temperature and heated at 80° C. for 4 h. The reaction mixture was cooled to 0° C. and quenched with water (20 mL) dropwise. The insoluble inorganics was filtered through CELITE®. The filtrate was dried over Na2SO4, filtered, concentrated to afford 1,2,3,4-tetrahydroquinoxaline (36 g, 268 mmol, 80% yield). NMR: 1H NMR (400 MHz, CDCl3) δ ppm 6.6 (2H, m), 6.5 (2H, m), 3.65 (2H, bs), 3.40 (4H, s).

Workup

  1. temperatureheated at 80° C. for 4 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with water (20 mL) dropwise
  4. filtrationThe insoluble inorganics was filtered through CELITE®
  5. dry with materialThe filtrate was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a3bc6147cf8d4af9b692dd4179a96bec
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

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