Methyl 3-isoquinolinecarboxylate

Methyl 3-isoquinolinecarboxylate Property

Melting point:

86-88 °C (lit.)

Boiling point:

321.94°C (rough estimate)

Density 

1.1963 (rough estimate)

refractive index 

1.4900 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder

pka

2.58±0.30(Predicted)

Appearance

Off-white to light yellow Solid

BRN 

473630

InChI

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

InChIKey

ZBCGBIZQNMVMPC-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC=C2)C=C(C(OC)=O)N=1

CAS DataBase Reference

27104-73-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Methyl 3-isoquinolinecarboxylate Chemical Properties,Usage,Production

Chemical Properties

Cream powder

Uses

Methyl 3-isoquinolinecarboxylate was used in the preparation of 3-acetylisoquinoline.

Definition

ChEBI: Methyl isoquinoline-3-carboxylate is a member of isoquinolines.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 1081, 1982 DOI: 10.1021/jm00351a015

Synthesis

General procedure for the synthesis of methyl isoquinoline-3-carboxylate from methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate: In a 250 mL aubergine vial, (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (2) (4.23 g, 22.15 mmol) and N,N-dimethylformamide (50 mL) were added. Subsequently, potassium permanganate (2.97 g, 18.79 mmol) was added to the solution. After the reaction was carried out for 6 hours, ethanol (50 mL) was added and stirred for 30 minutes. After that, the solvent was removed and the residue was dissolved with methanol (30 mL). Finally, the residue was purified by column chromatography to give a colorless solid product (858 mg, 24.56% yield).

References

[1] RSC Advances, 2017, vol. 7, # 77, p. 48848 - 48852
[2] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 34, p. 8957 - 8965
[3] Patent: CN106986825, 2017, A. Location in patent: Paragraph 0023; 0031; 0032