Hexane → Methyl 2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoate

HRID 2367090Notes

Reaction equation

HRID 2367090 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:22]([C:24]2[CH:39]=[CH:38][CH:37]=[CH:36][C:25]=2[C:26]([O:28][CH2:29]C2C=CC=CC=2)=[O:27])=[O:23])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][C:12](=[O:21])OCC1C=CC=CC=1)([O-])=O.C[Si](C=[N+]=[N-])(C)C.CCCCCC>O1CCCC1.C(OCC)(=O)C.C1(CO)C=CC=CC=1>[O:21]=[C:12]1[NH:1][C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:22]([C:24]3[CH:39]=[CH:38][CH:37]=[CH:36][C:25]=3[C:26]([O:28][CH3:29])=[O:27])=[O:23])[CH:5]=2)[NH:10][CH2:11]1

Participants

6

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 67045250Phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate

Product 1

HCID 67044874Methyl 2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoateYield 67%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A solution of phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate (0.31 g, 0.59 mmol) in a mixture of tetrahydrofurane-ethyl acetate (1:1, 50 mL) was hydrogenated in the presence of 10% Pd/C (0.15 g) in a Parr shaker at 40 psi, until the consumption of hydrogen ceased. The catalyst was filtered off and the solvent was evaporated. The resulting crude product was converted into its methyl ester in a mixture of benzene-methanol (9:1, 5.0 mL) by the addition of 2.0 M trimethylsilyldiazomethane solution in hexane (0.3 mL, 0.60 mmol). The reaction was quenched by the addition of a few drops of acetic acid and the solvent was evaporated. The resulting crude product was purified by silica gel flash chromatography (hexane:ethyl acetate 4:1 to 1:1 eluent) to give methyl 2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoate (0.12 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): 8.06 (s, 1H), 7.83 (dd, 1H), 7.64 (d, 1H), 7.52 (t, 1H), 7.38 (d, 1H), 7.09 (7.03 (d, 1H), 4.41 (s, 2H), 3.77 (s, 3H); MS (EI) for C17H14N2O4: 311 (MH+).

Workup

  1. customwas hydrogenated in the presence of 10% Pd/C (0.15 g) in a Parr shaker at 40 psi, until the consumption of hydrogen
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated
  4. customThe reaction was quenched by the addition of a few drops of acetic acid
  5. customthe solvent was evaporated
  6. customThe resulting crude product was purified by silica gel flash chromatography (hexane:ethyl acetate 4:1 to 1:1 eluent)

Sources & evidence

ORD record
ord-4d1166e7edf842e6b1b9a3d3e1174b98
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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