Isoquinolin-5-ol → 2-[4,4-Bis-(4-fluorophenyl)butyl]-5-hydroxyisoquinolinium bromide

HRID 963982Notes

Reaction equation

HRID 963982 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.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:20][CH2:21][CH2:22][Br:23])=[CH:15][CH:14]=1>>[Br-:23].[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:20][CH2:21][CH2:22][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:17][CH:18]=1

Participants

3

Reactant 2

HCID 30386Isoquinolin-5-olHCID 937631,1'-(4-Bromobutylidene)bis[4-fluorobenzene]

Product 1

HCID 158708912-[4,4-Bis-(4-fluorophenyl)butyl]-5-hydroxyisoquinolinium bromide

Conditions

Temperature
80 °C

Procedure

A mixture of 5-hydroxyisoquinoline (4.56 g, 31.41 mmol) and 4,4-bis(4-fluorophenyl)butyl bromide (11.40 g, 35.06 mmol. Prepared according to the procedure of Miroslav Rajsner, et al., Czech. Collect. Czech. Chem. Commun., 1978;43:1760) in 100 mL of anhydrous DMF was stirred at 80° C. overnight. The reaction mixture was cooled to 0° C. Ethyl acetate (400 mL) was added to precipitate product. The solid was collected by filtration and washed with ethyl acetate (2×100 mL). The solid was air-dried to give 10.74 g of product as an off-white solid.

Workup

  1. customPrepared
  2. customCollect
  3. temperatureThe reaction mixture was cooled to 0° C
  4. additionEthyl acetate (400 mL) was added
  5. customto precipitate product
  6. filtrationThe solid was collected by filtration
  7. washwashed with ethyl acetate (2×100 mL)
  8. customThe solid was air-dried

Sources & evidence

ORD record
ord-709147a52d124a7b9b8ef1ecf1ac8405
Source dataset
uspto-grants-1998_06
Patent number
US05767129

Reaction notes

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