Acetic Anhydride → HCID 86642929, compound

HRID 1802085Notes

Reaction equation

HRID 1802085 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N+:15]([O-])=[CH:14][CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(OC(=O)C)(=O)C.[N+:27]([CH:30]([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32])([O-:29])=[O:28]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:30]([N+:27]([O-:29])=[O:28])([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 97978Propanoic acid, 2-nitro-, ethyl esterHCID 67408090HCID 67408090, compound

Product 1

HCID 86642929HCID 86642929, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of 6-Heptyloxy-quinoline 1-oxide (500 mg, 0.002 mol) and acetic anhydride (0.255 mL, 0.00270 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was added to a solution of ethyl 2-nitropropionate (284 mg, 0.00193 mol) in DMF (2 mL) at at 23° C. dropwise. The reaction mixture was then stirred at 23° C. for 12 hours. The reaction mixture was then heated at 50° C. for 6 hours. Solvent was removed under vacuum, and the residue was treated with Na2CO3 (sat), and DCM. Organic layer was collected, and dried over Na2SO4. The mixture was then purified via chromatography (SiO2, 24 g, ethyl acetate/hexanes 0-35%) to give a pure product 523 mg (70%). 1H NMR (CHLOROFORM-d) δ: 8.09 (d, J=8.5 Hz, 1H), 7.95 (d, J=9.0 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.39 (dd, J=9.3, 2.5 Hz, 1H), 7.08 (d, J=2.5 Hz, 1H), 4.40 (q, J=7.0 Hz, 2H), 4.09 (t, J=6.5 Hz, 2H), 2.40 (s, 3H), 1.82-1.93 (m, 2H), 1.45-1.56 (m, 2H), 1.26-1.44 (m, 9H), 0.92 (t, J=6.7 Hz, 3H). MS (M+1): 389.30.

Workup

  1. temperatureThe reaction mixture was then heated at 50° C. for 6 hours
  2. customSolvent was removed under vacuum
  3. additionthe residue was treated with Na2CO3 (sat), and DCM
  4. customOrganic layer was collected
  5. dry with materialdried over Na2SO4
  6. customThe mixture was then purified via chromatography (SiO2, 24 g, ethyl acetate/hexanes 0-35%)

Sources & evidence

ORD record
ord-d18159d8512c4a73a7a697607fb49d5c
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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