Methyl 5-hydroxynicotinate

Light beige powder and lumps

Method A. Step A. Methyl 5 -hydroxynicotinate. To a solution of 5-hydroxynicotinic acid (833 g, 5.99 mol) in methanol (6.7 L) was added HEXAMPLE 36A. General procedure: 4-Hydroxypicolinic acid 3 (348 mg, 2.5 mmol) was added to methanol (25 mL), and then concentrated sulfuric acid (0.2 mL). The mixture was refluxed for 20 h, then the solvent was evaporated under vacuum. The residue was neutralized with saturated aqueous sodium bicarbonate solution, extracted with DCM/MeOH (10/1, 5×30 mL), dried over anhydrous NaSynthesis of methyl 5-hydroxynicotinateO OHSOCI2 MeOHHO HO UNTo a stirred solution of 5-hydroxynicotinic acid (10 g, 71 .9 mmol) in MeOH (100 mL)was added sulfurous dichloride (1 mL) drop wise over 5mm The resulting mixturewas stirred at room temperature overnight. The resulted solution was added 100 mLof NaHCO3.The precipitate was filtrated and washed with MeOH for several cycles togive 8.5 g of A031 -2 (75percent yields), which was used for the nest step without furtherpurification.To a stirred solution of 5-hydroxynicotinic acid (10 g, 71.9 mmol) in MeOH (100 mL) was added sulfurous dichloride (1 mL) drop wise over 5 min. The resulting mixture was stirred at room temperature overnight. The resulted solution was added 100 mL of NaHCOTo a stirred solution of 5-hydroxynicotinic acid (10 g, 71 .9 mmol) in MeOH (100 mL) was added sulfurous dichloride (1 mL) drop wise over 5 min. The resulting mixture was stirred at room temperature overnight. The resulted solution was added 100 mL of NaHCOs.The precipitate was filtrated and washed with MeOH for several cycles to give 8.5 g (75percent yields), which was used for the next step without further purification.To a stirred solution of 5-hydroxynicotinic acid (10 g, 71.9 mmol) in MeOH (100 mL) was added sulfurous dichloride (1 mL) drop wise over 5 min. The resulting mixture was stirred at room temperature overnight. The resulted solution was added 100 mL of NaHCOA mixture of 5-hydroxynicotinic acid (3 g, 21.6 mmol), cone H2SO4 (2.2 g, 21.6 mmol) in MeOH (50 mL) was heat at 70 °C overnight. The mixture was concentrated, poured into water (100 mL) and extracted with EA (100 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford methyl 5-hydroPreparation of Compound A29A mixture of compound A28 (25.0 g, 180 mmol) and concentrated H[0444] Preparation of compound A29: A mixture of compound A28 (25.0 g, 180 mmol) and concentrated HThionyl chloride (780 jil, 10.7 mmol) was added drop-wise to a suspension of 5- hydroxynicotinic acid (497 mg, 3.57 mmol) in MeOH (5 ml) at ambient temperature. The mixture was heated at 60 °C overnight. 0.1 M Potassium phosphate buffer (pH 7) (50 ml) was added and the mixture extracted with EtOAc. The combined organic layers were dried(Mg504). Yield: 354 mg (65percent); white solid.

Molecular Weight:153.14
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:59.4
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes