Diphenyl Ether → 7-Bromoisoquinolin-1-ol

HRID 2068592Notes

Reaction equation

HRID 2068592 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7]C(N=[N+]=[N-])=O)=[CH:4][CH:3]=1.C([N:19]([CH2:24]CCC)CCCC)CCC.C1([O:34]C2C=CC=CC=2)C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]=[CH:7][NH:19][C:24]2=[O:34])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 7583Diphenyl EtherHCID 7622TributylamineHCID 539034244-Bromocinnamoyl azide

Product 1

HCID 112761337-Bromoisoquinolin-1-olYield 30%

Procedure

A solution of compound 4 (121.6 g, 0.48 mol) and tributylamine (177.9 g, 0.96 mol) in diphenylether (1.2 L) was headed to 210° C. for 2 hours under N2. Then the mixture was cooled to room temperature, the precipitate was filtered, washed with hexane, and dried to give 5 (32 g, 30%)

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with hexane
  3. customdried

Sources & evidence

ORD record
ord-0bb9fed4f6fa4adc9412152eb85090d3
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

Loading…