2-Methyl-6-quinolinecarboxylic acid Chemical Properties

Melting point:

250 °C

Boiling point:

347.6±27.0 °C(Predicted)

Density 

1.285±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.13±0.30(Predicted)

form 

Solid

color 

White to Light yellow to Light orange

InChI

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

InChIKey

IZONZQFTYGVOOO-UHFFFAOYSA-N

SMILES

N1C2C(=CC(C(O)=O)=CC=2)C=CC=1C

CAS DataBase Reference

635-80-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

Hazard Note 

Irritant

HS Code 

29334900

2-Methyl-6-quinolinecarboxylic acid Usage And Synthesis

Chemical Properties

White solid

Uses

2-Methylquinoline-6-carboxylic Acid is a preparation of arylpyrazolopyridine derivative as monoacylglycerol lipase modulators.

Synthesis

General procedure for the synthesis of 2-methyl-6-quinoline carboxylic acid from p-aminobenzoic acid and trans-2-butenal: Intermediate 13: Synthesis of (2-methylquinolin-6-yl)methylamine: Step 1: Preparation of 2-methylquinoline-6-carboxylic acid: 6N hydrochloric acid (73 ml) was added to 4-aminobenzoic acid (5 g, 36.45 mmol) and heated to reflux for 2 hours. Subsequently, crotonaldehyde (3.06 g, 43.75 mmol) was added slowly and dropwise over 45 min. After 12 hours of reaction, the reaction mixture was cooled to 0 °C and the pH was adjusted to 3-5 with aqueous ammonia solution. the aqueous phase was extracted with dichloromethane, the organic phases were combined and acidified with 2N hydrochloric acid, the precipitate was collected by filtration and dried under vacuum to afford 2-methyl-6-quinolinecarboxylic acid as a brown solid (3.0 g, 44% yield).

References

[1] Patent: WO2013/144737, 2013, A2. Location in patent: Paragraph 252
[2] Patent: US2015/57309, 2015, A1. Location in patent: Paragraph 0524
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4647 - 4654
[4] Chemistry - A European Journal, 2018, vol. 24, # 61, p. 16368 - 16378
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6138 - 6141

2-Methyl-6-quinolinecarboxylic acid(635-80-3)Related Product Information

• QUINOLINE-4-CARBOXYLIC ACID
• Isoquinoline
• o-Toluic acid
• 4-Bromomethylbenzoic acid
• Methylparaben
• Bensulfuron methyl
• 4-(Aminomethyl)benzoic acid
• p-Toluic acid
• 4-(Chloromethyl)benzoic acid
• Kresoxim-methyl
• 8-Hydroxyquinoline
• Quinclorac
• Methyl acrylate
• 3-(Trifluoromethyl)benzoic acid
• quinolinium hydrogen sulphate
• Quinhydrone
• Quinaldic acid
• Thiophanate-methyl