N-methyl-2-pyrrolidone → tert-butyl 4-(4-cyanophenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate

HRID 551816Notes

Reaction equation

HRID 551816 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCCC1=O.F[C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.CC(C)([O-])C.[K+]>O>[C:30]([C:29]1[CH:32]=[CH:33][C:26]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)=[CH:27][CH:28]=1)#[N:31]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 145174-FluorobenzonitrileHCID 16740533Tert-butyl 1,2,3,4-tetrahydroquinoxaline-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67188179tert-butyl 4-(4-cyanophenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylateYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester, 10 ml of N-methylpyrrolidinone, 0.57 g of 4-fluorobenzonitrile and 0.96 g of potassium tert-butoxide are introduced into a 20 ml glass tube. The reaction medium is stirred for 5 min, water is added and extraction is carried out 3 times with diethyl ether. The organic phases are combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a gradient of ethyl acetate from 3.5% to 35% in heptane. 0.9 g of tert-butyl 4-(4-cyanophenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate is obtained.

Workup

  1. extractionextraction
  2. washwashed with water
  3. dry with materialwith a saturated aqueous sodium chloride solution, dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel
  6. washeluted with a gradient of ethyl acetate from 3.5% to 35% in heptane

Sources & evidence

ORD record
ord-3133cda619e44f74be159dfec2aa06dd
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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