5-BROMOISOQUINOLIN-1(2H)-ONE Chemical Properties

Boiling point:

443.2±45.0 °C(Predicted)

Density 

1.620

storage temp. 

Sealed in dry,Room Temperature

pka

12.19±0.20(Predicted)

form 

solid

color 

Light yellow to light brown

InChI

InChI=1S/C9H6BrNO/c10-8-3-1-2-7-6(8)4-5-11-9(7)12/h1-5H,(H,11,12)

InChIKey

UKIWLFJYNMJPEG-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(Br)=CC=C2)C=CN1

Safety Information

HS Code 

2933499090

5-BROMOISOQUINOLIN-1(2H)-ONE Usage And Synthesis

Synthesis

5-Bromo-3,4-dihydroisoquinolin-1(2H)-one (4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (8.6 g, 37.9 mmol) were mixed in 1,4-dioxane (76 mL). The reaction mixture was stirred at 100 °C for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was dissolved in ethyl acetate (500 mL) and washed with 10% aqueous sodium hydroxide solution (2 x 500 mL). The organic and aqueous layers were separated and the aqueous layer was further extracted with ethyl acetate (4 x 300 mL). All organic layers were combined and dried with anhydrous sodium sulfate, then concentrated by evaporation. The product was purified by fast chromatography with the eluent being a solvent mixture of dichloromethane and methanol (ratio tapered from 99:1 to 96:4) to afford 5-bromoisoquinolin-1(2H)-one (1.49 g, 6.65 mmol, 35% yield) as a yellow solid. The product was analyzed by LCMS showing a purity of 94% with a retention time (Rt) of 1.243 min, and electrospray mass spectrometry (ESMS) showed a molecular ion peak m/z of 224 ([M+H]+).

References

[1] Patent: WO2014/153055, 2014, A2. Location in patent: Paragraph 0120-0121
[2] Patent: WO2015/20553, 2015, A1. Location in patent: Paragraph 00113-00114
[3] Patent: WO2015/50471, 2015, A1. Location in patent: Paragraph 00107; 00108
[4] Patent: WO2015/50472, 2015, A1. Location in patent: Paragraph 00111; 00112

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