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

HRID 2281873Notes

Reaction equation

HRID 2281873 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 (100 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 light 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-cf022990348444c6b94ba543b90a7c68
Source dataset
uspto-grants-2015_09
Patent number
US09139587B2

Reaction notes

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