Diphenyl Ether → HCID 178434741, compound

HRID 1042978Notes

Reaction equation

HRID 1042978 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:20])=[C:12](C([O-])=O)[CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:21])[O:4][N:3]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:20])=[CH:12][CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:21])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 1784347427-(3,5-Dimethyl-4-isoxazolyl)-4-hydroxy-3-quinolinecarboxylate2×

Product 1

HCID 178434741HCID 178434741, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

7-(3,5-dimethyl-4-isoxazolyl)-4-hydroxy-3-quinolinecarboxylate (for a preparation see Intermediate 9, 10 g, 35.21 mmol) was suspended by small portions to boiling diphenyl ether (200 ml) and allowed to reflux for 2 h. The reaction mixture was poured into hexane (500 ml) at 0° C., the precipitate was filtered and washed several times with hexane to give the title compound as a white solid (6.8 g, 86%). [APCI-MS] m/z: 240 MH+, Rt 1.89 min. 1H NMR (300 MHz, CDCl3, ppm) δ: 12.44 (brs, 1H), 8.67 (d, J=8.5 Hz, 1H), 8.10 (d, J=7.2 Hz, 1H), 7.80 (s, 1H), 7.62-7.55 (m, 1H), 7.25 (d, J=8.5 Hz, 1H), 6.61 (d, J=7.4 Hz, 1H), 2.64 (s, 3H), 2.49 (s, 3H).

Workup

  1. temperatureto reflux for 2 h
  2. filtrationthe precipitate was filtered
  3. washwashed several times with hexane

Sources & evidence

ORD record
ord-8debf97bc31c424484c60622d4efdd76
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

Loading…