HCID 69234700, compound → HCID 69235848, compound

HRID 716847Notes

Reaction equation

HRID 716847 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[C:9]2[CH:8]=[C:7]3[O:22][CH2:23][O:24][C:6]3=[CH:5][C:4]=2[N:3]=1>O1CCOCC1.[Pd]>[CH3:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[C:9]2[CH:8]=[C:7]3[O:22][CH2:23][O:24][C:6]3=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 69234700HCID 69234700, compound

Product 1

HCID 69235848HCID 69235848, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-methyl-8-(4-nitrophenoxy)[1,3]dioxolo[4,5-g]quinoline (2.0 g, 6.18 mmol) in dioxane (100 mL) and 10% Pd/C (500 mg) was hydrogenated for 7 h at 35 psi. The reaction mixture was filtered through a pad of Celite and the filter cake was washed with dioxan. The combined filtrate and washings was evaporated in vacuo to dryness. The solid residue recrystallized from CHCl3 to yield 4-[(6-methyl[1,3]dioxolo-[4,5-g]quinolin-8-yl)oxy]phenylamine, 1.680 g (92.43%); mp 251-253° C.; 1H NMR (DMSO-d6) δ 2.43 (3H, s, Me), 5.56 (2H, brs, exchangeable, NH2), 6.21 (2H, s, CH2), 6.32 (1H, s, ArH), 6.66 (2H, d, J=8.6 Hz, ArH), 6.90 (2H, d, J=8.6 Hz, ArH), 7.28 (1H, s, ArH), 7.49 (1H, s, ArH). Anal. Calcld. for (C17H14N2O3): C, 69.38; H, 4.79; N, 9.25. Found: C, 69.57; H, 4.88; N, 9.32.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with dioxan
  3. customThe combined filtrate and washings was evaporated in vacuo to dryness
  4. customThe solid residue recrystallized from CHCl3

Sources & evidence

ORD record
ord-9ca9545d1d4544a9b17d67584110d1b1
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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