Hydrochloric Acid → 4-(4-Nitrophenoxy)quinolin-7-ol

HRID 2277383Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl>O1CCOCC1>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=3)[N:16]=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 7-(benzyloxy)-4-(4-nitrophenoxy)quinoline (10.85 g, 29.14 mmol) and 1,4-dioxane (38 mL) was added concentrated hydrochloric acid (38 mL). The reaction was stirred in an oil bath at 100° C. for 9 hours, monitored by TLC and LC-MS. After the complete consumption of 7-(benzyloxy)-4-(4-nitrophenoxy)quinoline, the mixture was cooled to room temperature. The solid was collected and stirred in 95% EtOH (30 mL) for 2 hours. The title compound was collected by filtration as a beige solid (8.25 g, 88.7%).

Workup

customAfter the complete consumption of 7-(benzyloxy)-4-(4-nitrophenoxy)quinoline
temperaturethe mixture was cooled to room temperature
customThe solid was collected
stirringstirred in 95% EtOH (30 mL) for 2 hours
filtrationThe title compound was collected by filtration as a beige solid (8.25 g, 88.7%)

Sources & evidence

ORD record: ord-cbc0f1c5ae8f4ff2909e68e4f1fc09a9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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