Ethyl Acetate → 2-(4,4-Diphenylbutyl)-5-hydroxyisoquinolinium bromide

HRID 963980Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Br:12][CH2:13][CH2:14][CH2:15][CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>CN(C=O)C>[Br-:12].[C:17]1([CH:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:15][CH2:14][CH2:13][N+:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[OH:1])[CH:7]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-hydroxyisoquinoline (2.17 g, 14.95 mmol) and 1-bromo-4,4-diphenylbutane (4.79 g, 16.56 mmol) in 75 mL of anhydrous DMF was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature. Ethyl acetate (200 mL) was added to precipitate product. The solid was collected by filtration and washed with ethyl acetate (1×70 mL). The solid was air-dried to give 4.52 g of product as an off-white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customto precipitate product
filtrationThe solid was collected by filtration
washwashed with ethyl acetate (1×70 mL)
customThe solid was air-dried

Sources & evidence

ORD record: ord-cdcbb52ef3a04fea8042aa5de75d6e0d
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767129

Reaction notes

Loading…