3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI)

3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI) Property

Boiling point:

135 °C(Press: 10 Torr)

Density 

1.055±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

13.77±0.20(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933399990

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

3-Pyridinemethanol,alpha,6-dimethyl-(6CI,9CI) Chemical Properties,Usage,Production

Uses

5-(1-Hydroxyethyl)-2-methylpyridine is an intermediate used in the synthesis of metabolites of the antidiabetic, antihyperglycemic agent Pioglitazone (P471000).

Synthesis

General procedure for the synthesis of 6-methyl-3-(1-hydroxyethyl)pyridine from 1-(6-methylpyridin-3-yl)ethanone: Sodium borohydride (2.3 g, 0.06 mol) was added in batches to a solution of 1-(6-methylpyridin-3-yl)ethanol (160 ml) of 1-(6-methylpyridin-3-yl)ethanone (16.4 g, 0.121 mol) at 30 °C, maintaining a constant temperature and continuously stirring the reaction mixture. After 1 hour of reaction, the reaction mixture was diluted with saturated sodium bicarbonate solution (2 x 200 ml) and subsequently extracted with dichloromethane (2 x 500 ml). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give a light yellow oil. The crude product was purified by fast column chromatography (eluent: 5% methanol/dichloromethane) to afford 6-methyl-3-(1-hydroxyethyl)pyridine (17.0 g, two-step yield 93%) as a pale yellow oil.ES-MS [M + 1]+ : 138.1. 1H NMR (400 MHz, CDCl3): δ 8.35 (d, J = 2.0 Hz, 1H), δ 7.63 (dd, J = 8.0,2.4 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (brs, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H).

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 26, p. 5053 - 5063
[2] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 12, p. 2168 - 2172
[3] Chemische Berichte, 1947, vol. 80, p. 502,505
[4] Patent: WO2009/80637, 2009, A1. Location in patent: Page/Page column 32
[5] Patent: WO2015/150476, 2015, A1. Location in patent: Page/Page column 23; 24