Acetic Acid → HCID 68606297, compound

HRID 1802086Notes

Reaction equation

HRID 1802086 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]([N+:26]([O-])=O)([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)(=O)C>[Zn]>[NH2:26][C:19]([C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:10]=2)[N:15]=1)([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86642929HCID 86642929, compound

Product 1

HCID 68606297HCID 68606297, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
10 °C

Procedure

Ethyl 2-(6-heptyloxyquinolin-2-yl)-2-nitropropanoate (325.0 mg, 0.0008366 mol) was dissolved in acetic acid (5 mL, 0.09 mol), and cooled to at 10° C., followed by zinc (547.1 mg, 0.008366 mol;) in very small portions to keep the temperature constant. The reaction mixture was then allowed to stir for additional for 5 hours, and filtered through a Celite pad. The excess is of solvents were removed under vacuum, and the residue was purified via HPLC (10-100% acetonitrile with 0.1% formic acid) to give a pure product (57.0 mg, 14%). 1H NMR (CHLOROFORM-d) δ: 8.05 (d, J=8.5 Hz, 1H), 7.94 (d, J=9.3 Hz, 1H), 7.57 (d, J=8.5 Hz, 1H), 7.36 (dd, J=9.3, 2.5 Hz, 1H), 7.06 (d, J=2.5 Hz, 1H), 4.20 (q, J=7.0 Hz, 2H), 4.07 (t, J=6.5 Hz, 2H), 1.77-1.93 (m, 5H), 1.44-1.57 (m, 2H), 1.28-1.44 (m, 6H), 1.22 (t, J=7.2 Hz, 3H), 0.90 (t, J=6.8 Hz, 3H). MS (M+1): 359.30.

Workup

  1. filtrationfiltered through a Celite pad
  2. customwere removed under vacuum
  3. customthe residue was purified via HPLC (10-100% acetonitrile with 0.1% formic acid)

Sources & evidence

ORD record
ord-05fcdc1cc5d048a5b806e845ea75bf67
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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