2(1H)-Pyridinone,4-(hydroxymethyl)-(9CI)

2(1H)-Pyridinone,4-(hydroxymethyl)-(9CI) Property

Melting point:

144-145 °C

Boiling point:

428.0±27.0 °C(Predicted)

Density 

1.225±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

11.67±0.10(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P321Specific treatment (see … on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

2(1H)-Pyridinone,4-(hydroxymethyl)-(9CI) Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-(hydroxymethyl)pyridin-2(1H)-one from methyl 2-hydroxypyridine-4-carboxylate: to an anhydrous tetrahydrofuran (23 mL) suspension of methyl 2-methoxy-1,2-dihydro-4-pyridinecarboxylate (1.37 g, 8.98 mmol) was added slowly and dropwise 2 M lithium borohydride/tetrahydrofuran solution (22.5 mL, 45 mmol). The reaction mixture was heated to 55 °C and maintained for 3.5 h under nitrogen protection. Upon completion of the reaction, methanol (15 mL) and water (3 mL) were carefully added, followed by stirring for 30 min at room temperature. The mixture was concentrated and methanol (10 mL) was again carefully added. After continued stirring for 30 min, the mixture was adsorbed onto silica gel and purified by silica gel column chromatography using a 0 to 30% methanol-dichloromethane gradient elution to afford the target product, 4-(hydroxymethyl)pyridin-2(1H)-one, as an off-white solid (0.99 g, 88% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 11.29 (br s, 1H), 7.23 (d, J = 6.7 Hz, 1H), 6.21 (s, 1H), 6.03 (dd, J = 6.7, 1.3 Hz, 1H), 5.27 (t, J = 5.9 Hz, 1H), 4.28 (d, J = 5.9 Hz, 2H).

References

[1] Patent: WO2009/76387, 2009, A1. Location in patent: Page/Page column 30
[2] Patent: WO2014/31936, 2014, A2. Location in patent: Paragraph 0344; 0345
[3] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 1, p. 288 - 290
[4] Patent: US2003/220241, 2003, A1