Acetic Acid → 4-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester

HRID 1711221Notes

Reaction equation

HRID 1711221 reaction equation
C([O:3][C:4](=O)[C:5](=[O:30])[CH:6]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:16]=1[N+:27]([O-])=O)[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])C.C(O)(=O)C>C1COCC1.C(Cl)Cl.[Cl-].[Na+].O.[Zn]>[CH2:12]([O:11][C:9]([C:8]1[O:30][C:5]2[C:4](=[O:3])[NH:27][C:16]3[C:17]([N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:18][CH:19]=[CH:20][C:15]=3[C:6]=2[CH:7]=1)=[O:10])[CH3:13]

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 597967863-(2-Nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester

Product 1

HCID 597967744-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3-(2-nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid diethyl ester (iii) in THF is treated with acetic acid (“HOAc”) and is stirred at room temperature for 4 h. The reaction is treated with zinc dust (10 eq) and is stirred for an additional 2 h. The reaction is diluted with DCM, half saturated brine, and partitioned. The organic layer is washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated. Chromatography gives 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester (iv).

Workup

  1. stirringis stirred for an additional 2 h
  2. custompartitioned
  3. washThe organic layer is washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fbb0fcc091174b98a634fe524b57f1c4
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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