ISOQUINOLINE-1-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Density 

1.210

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C11H9NO2/c1-14-11(13)10-9-5-3-2-4-8(9)6-7-12-10/h2-7H,1H3

InChIKey

WJHGJDGITRCZLH-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)C2=C(C=CC=C2)C=CN=1

Safety Information

HS Code 

2933499090

ISOQUINOLINE-1-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Synthesis

To a solution of isoquinoline-1-carboxylic acid (10 g, 57.74 mmol) in methanol (150 mL) was slowly added concentrated sulfuric acid (15 mL) at 0 °C. The reaction mixture was gradually warmed to 65 °C and stirred continuously at this temperature for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature. Subsequently, the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give methyl isoquinoline-1-carboxylate as a yellow oil product (11.2 g, 100% yield). The product was analyzed by ESI-MS and the m/z [M + H]+ was 188.

References

[1] Patent: US2014/256734, 2014, A1. Location in patent: Paragraph 0201-0203
[2] Organic Letters, 2005, vol. 7, # 17, p. 3609 - 3612
[3] Polyhedron, 2016, vol. 109, p. 147 - 153

ISOQUINOLINE-1-CARBOXYLIC ACID METHYL ESTER(27104-72-9)Related Product Information

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