5-METHOXYPYRAZINE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

197.5-199.5℃

Boiling point:

296.8±35.0 °C(Predicted)

Density 

1.371±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.18±0.10(Predicted)

form 

Solid

color 

Light yellow to Brown to Dark green

InChI

InChI=1S/C6H6N2O3/c1-11-5-3-7-4(2-8-5)6(9)10/h2-3H,1H3,(H,9,10)

InChIKey

YVGVOPNUEFTVQO-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=C(OC)N=C1

Safety Information

WGK Germany 

WGK 3

HS Code 

2933998090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

5-METHOXYPYRAZINE-2-CARBOXYLIC ACID Usage And Synthesis

Synthesis

Step 2: Preparation of 5-methoxypyrazine-2-carboxylic acid To a solution of 5-chloropyrazine-2-carboxylic acid (7 g, 44.15 mmol) in methanol (55 mL) was added concentrated sulfuric acid (0.4 mL) and heated to reflux for 4 hours at 65 °C. Upon completion of the reaction, the reaction mixture was cooled to room temperature and diluted with methanol (15 mL). Subsequently, a methanolic solution of sodium methanolate (8.58 g, 158.94 mmol, 35 mL) was slowly added and the reaction mixture was stirred for 30 min at room temperature. Next, a 30 mL aqueous solution of sodium hydroxide (2.825 g, 70.643 mmol) was added to the reaction mixture, followed by 40 mL of water. The reaction mixture was heated at 40 °C for 1 h, followed by concentration under reduced pressure to remove methanol. The residue was diluted with water and the pH was adjusted to 2-3 with 38% aqueous hydrochloric acid and then extracted with ethyl acetate (600 mL x 3). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 5-methoxypyrazine-2-carboxylic acid (6.43 g, 94% yield) as an orange solid. Mass spectrometry analysis: calculated value [M + H]+: 155.04; measured value [M + H]+: 155.1.

References

[1] Patent: WO2015/48507, 2015, A1. Location in patent: Paragraph 0171

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