m-Chloroperbenzoic acid → 7-(methyloxy)-8-[(phenylmethyl)oxy]quinoline-N-oxide

HRID 2188606Notes

Reaction equation

HRID 2188606 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N+:10]2[O-:29])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67057987HCID 67057987, compound

Product 1

HCID 690249747-(methyloxy)-8-[(phenylmethyl)oxy]quinoline-N-oxideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-(methyloxy)-8-[(phenylmethyl)oxy]quinoline (0.30 g; 1.13 mmol) and 77% by weight m-chloroperbenzoic acid (0.38 g; 1.69 mmol) are added in succession to dry CH2Cl2 (11 ml) at 4° C. under argon. The mixture is stirred for 48 hours at ambient temperature, then CH2Cl2 (40 ml) is added. The reaction medium is washed with a saturated aqueous solution of NaHCO3 (2×50 ml) and the solvent is evaporated under reduced pressure. The resulting oil is purified by silica gel chromatography, eluted with a CH2Cl2/CH3OH (95/5, v/v) mixture to yield 7-(methyloxy)-8-[(phenylmethyl)oxy]quinoline-N-oxide in the form of a yellow oil (0.18 g; 0.64 mmol, yield=58%). NMR-1H (250 MHz, CDCl3) δ, ppm: 8.43 (dd, 3J (H, H)=6.0 Hz, 4J ((H, H)=1.0 Hz, 1H); 7.68-7.58 (m, 4H); 7.41-7.30 (m, 4H); 7.10 (dd, 3J (H, H)=8.5 Hz, 3J (H, H)=6.0 Hz, 1H); 5.23 (s, 2H); 3.96 (s, 3H). NMR-13C (63 MHz, CDCl3) δ, ppm: 138.4; 128.9; 128.7; 128.2; 127.8; 127.6; 125.7; 124.9; 123.4; 119.5; 118.8; 116.8; 107.7; 75.2; 57.1. MS (CID, NH3): m/z=282 (MH+). Analysis (%) for C17H15NO3: calculated C, 72.58; H, 5.37; N, 4.98. found C, 72.74; H, 4.91; N, 4.87.

Workup

  1. washThe reaction medium is washed with a saturated aqueous solution of NaHCO3 (2×50 ml)
  2. customthe solvent is evaporated under reduced pressure
  3. customThe resulting oil is purified by silica gel chromatography
  4. washeluted with a CH2Cl2/CH3OH (95/5

Sources & evidence

ORD record
ord-0c0ec77145e84d95b3addde6167e0949
Source dataset
uspto-grants-2012_12
Patent number
US08324196B2

Reaction notes

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