Diphenyl Ether → 6-Bromoisoquinolin-1(2H)-one

HRID 1892573Notes

Reaction equation

HRID 1892573 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[N:10]=[C:11]=[O:12])[CH:3]=1.C(N(CCCC)CCCC)CCC.O(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:11](=[O:12])[NH:10][CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 7622TributylamineHCID 24895420HCID 24895420, compound

Product 1

HCID 158851826-Bromoisoquinolin-1(2H)-oneYield 30.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
210 °C

Procedure

A solution of (E)-1-bromo-3-(2-isocyanatovinyl)benzene (100 g, 0.44 mol) in toluene (200 mL) was added dropwise to a mixture of tributylamine 1100 mL) and oxydibenzene (500 mL) at 190° C. After the addition, the mixture was heated at 210° C. for another two hours. Thin layer chromatography (petroleum ether/ethyl acetate 1:1) indicated the reaction was complete. The mixture was cooled to room temperature, filtered, and the solid was washed with ethyl acetate (50 mL×3). The solid was dried under vacuum to give crude 6-bromoisoquinolin-1(2H)-one (30 g, 30%) as a tight yellow solid, which was used in the next step directly.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washthe solid was washed with ethyl acetate (50 mL×3)
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-08ad48070f2b463ba6c664126c143542
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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