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

HRID 2404254Notes

Reaction equation

HRID 2404254 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 coded 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. customwas coded 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-ec882e54ad284844b221cfa4eec3a507
Source dataset
uspto-grants-2014_08
Patent number
US08802690B2

Reaction notes

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