| Identification | More | [Name]
Methyl 6-(hydroxymethyl)nicotinate | [CAS]
56026-36-9 | [Synonyms]
6-HYDROXYMETHYL-NICOTINIC ACID METHYL ESTER
METHYL 6-(HYDROXYMETHYL)NICOTINATE
6-Hydroxymethyl-Nicotinic | [Molecular Formula]
C8H9NO3 | [MDL Number]
MFCD00643821 | [Molecular Weight]
167.16 | [MOL File]
56026-36-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
75-78℃ | [Boiling point ]
293.4±30.0 °C(Predicted) | [density ]
1.244±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
13.20±0.10(Predicted) | [color ]
White to Orange to Green | [InChI]
InChI=1S/C8H9NO3/c1-12-8(11)6-2-3-7(5-10)9-4-6/h2-4,10H,5H2,1H3 | [InChIKey]
QVLONHSXRWCCAE-UHFFFAOYSA-N | [SMILES]
C1=NC(CO)=CC=C1C(OC)=O | [CAS DataBase Reference]
56026-36-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Synthesis]
Step 1. Synthesis of methyl 6-(hydroxymethyl)nicotinate (55): a mixture of methyl 2,5-pyridinedicarboxylate (54; 100.0 g, 0.51 mol), CaCl2 (227.4 g, 2.05 mol), and THF (1100 mL) was mixed with EtOH (1200 mL), and stirred for 30 min. NaBH4 (48.6 g, 1.28 mol) was added in batches at 0 °C. The reaction mixture was stirred at room temperature for 18 hours. Subsequently, saturated NH4Cl solution (1.5 L) and water (2.0 L) were added slowly and extracted with dichloromethane (3 x 3.0 L). The organic phases were combined, dried with MgSO4 and concentrated under reduced pressure to give methyl 6-(hydroxymethyl)nicotinate 55 (82.0 g, 96% yield). | [References]
[1] Patent: WO2010/56549, 2010, A1. Location in patent: Page/Page column 103
[2] Journal of Organic Chemistry, 2010, vol. 75, # 3, p. 650 - 659
[3] Inorganic Chemistry, 2015, vol. 54, # 22, p. 10542 - 10558
[4] Patent: US2010/16373, 2010, A1. Location in patent: Page/Page column 16
[5] Patent: US2016/256578, 2016, A1. Location in patent: Paragraph 0124; 0125 |
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