Diethyl Oxalate → Ethyl (1-acetyl-6-nitro-4-oxo-1,2,3,4-tetrahydroquinolin-3-yl)(oxo)acetate

HRID 1348920Notes

Reaction equation

HRID 1348920 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[C:7](=[O:17])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:28](OCC)(=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[C:7](=[O:17])[CH:6]([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2733832Lithium HexamethyldisilazideHCID 122491871-Acetyl-6-nitro-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 58859529Ethyl (1-acetyl-6-nitro-4-oxo-1,2,3,4-tetrahydroquinolin-3-yl)(oxo)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the material of Step 2 (4.8 g, 0.0205 mol) in THF (25 mL) at −78° C., was added the lithium bis(trimethylsilyl)amide (20.5 mL of a 1M in THF solution). The diethyl oxalate (3 g, d=1.076 g/mL, 2.8 mL, 0.0205 mol) was then added and the reaction mixture was allowed to warm to room temperature and stir overnight. The slurry was then filtered to give an orange solid. 6.1 g (MW=334.28 g/mol, 90% yield). LC/MS m/z=335 (m+1).

Workup

  1. filtrationThe slurry was then filtered
  2. customto give an orange solid

Sources & evidence

ORD record
ord-3363a8d3b0984f6ead10c2894a2082e1
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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