4-Nitrophenol → HCID 69234700, compound

HRID 1514814Notes

Reaction equation

HRID 1514814 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][O:14][C:8]3=[CH:7][C:6]=2[N:5]=[C:4]([CH3:15])[CH:3]=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(Cl)(Cl)Cl>[CH3:15][C:4]1[CH:3]=[C:2]([O:25][C:22]2[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=2)[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][O:14][C:8]3=[CH:7][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 3328638-chloro-6-methyl[1,3]dioxolo[4,5-g]quinoline

Product 1

HCID 69234700HCID 69234700, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of known 8-chloro-6-methyl[1,3]dioxolo[4,5-g]quinoline (2.216 g, 10 mmol)56 and 4-nitrophenol (2.08 g, 15 mmole) was heated at 140-150° C. for 2 h. The resulting solution was dissolved in chloroform and washed with 10% aq. solution of NaOH and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduce pressure. The resulting solid was collected by filtration, washed with ether and dried to 6-methyl-8-(4-nitrophenoxy)[1,3]dioxolo[4,5-g]quinoline, 2.94 g of (90.60%); mp 210-212° C.; 1H NMR (DMSO-d6) δ 2.52 (3H, s, Me), 6.21 (2H, s, CH2), 6.86 (1H, s, ArH), 7.30 (1H, s, ArH), 7.34-7.38 (3H, m, ArH), 8.29-8.33 (2H, m, ArH). Anal. Calcld. for (C17H12N2O5): C, 62.96; H, 3.73; N, 8.64. Found: C, 62.27; H, 3.84; N, 8.58.

Workup

  1. washwashed with 10% aq. solution of NaOH and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with ether
  6. dry with materialdried to 6-methyl-8-(4-nitrophenoxy)[1,3]dioxolo[4,5-g]quinoline, 2.94 g of (90.60%)

Sources & evidence

ORD record
ord-03dd506ba7a24213ad05062d76c76d0e
Source dataset
uspto-grants-2012_07
Patent number
US08222297B2

Reaction notes

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