2,7-Naphthalenediol → 7-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-2-ol

HRID 2115787Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:12].Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][CH:15]=1.[OH-].[K+]>CN1C(=O)CCC1.O.[Cu]>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:26][CH3:27])[N:17]=[CH:16][CH:15]=[C:14]2[O:12][C:2]1[CH:1]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([OH:11])=[CH:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of naphthalene-2,7-diol (8.95 g, 55.88 mmol) in NMP (50 mL) in a sealed tube, was added 4-chloro-6,7-dimethoxyquinoline (5.0 g, 22.35 mmol). KOH (1.40 g, 24.58 mmol) was added, followed by copper powder (0.71 g, 11.18 mmol). The tube was sealed and the solution was stirred and heated to 150° C. for 24 h. The reaction was cooled to RT, diluted with water and extracted with EtOAc 3×. The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography with 50% to 100% (95:5:0.5 EtOAc/MeOH/NH4OH) in Hexanes to give the titled compound. MS (ESI, pos. ion) m/z: 348.2 (M+1).

Workup

customThe tube was sealed
temperatureThe reaction was cooled to RT
extractionextracted with EtOAc 3×
washThe combined organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel chromatography with 50% to 100% (95:5:0.5 EtOAc/MeOH/NH4OH) in Hexanes

Sources & evidence

ORD record: ord-08da69a7bf1f43329271a38589a4cf58
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435823B2

Reaction notes

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