Diphenyl Ether → HCID 178487715, compound

HRID 588555Notes

Reaction equation

HRID 588555 reaction equation
O(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:22][CH:23]=[C:24]2[C:29](=[O:30])OC(C)(C)OC2=O)[CH:19]=[CH:20][CH:21]=1>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:19]([C:29]([OH:30])=[CH:24][CH:23]=[N:22]2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 7572485-[(3-Methoxyphenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 178487715HCID 178487715, compoundYield 30.2%

Procedure

To a solution of Ph2O (500 g) heated to 250° C. was added 108.7 g (392 mmol) of 5-[(3-Methoxyphenyl-amino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione in portions over a 30 min period. The mixture was heated an additional 15 min, cooled to rt, diluted with hexanes (800 mL) and the resulting slurry stirred overnite. The hexanes was decanted off, the solid residue dissolved in 600 mL of MeOH at reflux, cooled to rt and the resulting solid filtered and washed with minimal CH2Cl2. The analogous recrystallization procedure was followed to afford a total of 20.73 g (30%) of 7-methoxyquinolin-4-ol as a light brown solid. 1H NMR (methanol-d4) δ 3.87 (s, 3H), 6.23 d, J=7.3 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 6.96 (dd, J=9.0, 2.4 Hz, 1H), 8.11 (d, J=9 Hz, 1H); LC-MS (retention time: 0.77, method D), MS m/z 176 (M++1).

Workup

  1. temperatureThe mixture was heated an additional 15 min
  2. customThe hexanes was decanted off
  3. dissolutionthe solid residue dissolved in 600 mL of MeOH
  4. temperatureat reflux
  5. temperaturecooled to rt
  6. filtrationthe resulting solid filtered
  7. washwashed with minimal CH2Cl2
  8. customThe analogous recrystallization procedure

Sources & evidence

ORD record
ord-24265363588b4e5fad250c3ef9dc6c11
Source dataset
uspto-grants-2016_01
Patent number
US09227940B2

Reaction notes

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