Water → HCID 67328722, compound

HRID 1846163Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[C:3]1[CH:12]=[C:11]([OH:13])[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:14])[N:4]=1.[C:16](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C>[CH3:15][N:2]([CH3:1])[C:3]1[CH:12]=[C:11]([O:13][CH3:16])[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:14])[N:4]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution containing 689 mg (3.27 mmol) of methyl 6-(Dimethylamino)-4-hydroxy-2-methylnicotinate in 10 mL of anhydrous DMF were added 1.91 g (18.0 mmol) of anhydrous sodium carbonate followed by 611 μL (9.81 mmol) of methyl iodide. The reaction mixture was stirred at 23° C. for 16 h. Then, the reaction mixture was poured into 80 mL of water and extracted with two 80-mL portions of ethyl acetate. The combined organic solution was washed with one 80-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (3×10 cm). Elution with 1:1 hexanes-diethyl ether afforded the expected product as a white solid: yield 340 mg (47%); mp: 65-66° C.; silica gel TLC Rf 0.15 (1:1 hexanes-diethyl ether); 1H NMR (CDCl3) δ 2.37 (s, 3H), 3.07 (s, 6H), 3.80 (s, 3H) and 5.72 (s, 1H), 3.82 (s, 3H); 13C NMR (CDCl3) δ 168.4, 165.2, 160.3, 156.7, 107.6, 84.5, 55.2, 51.7, 37.8, 37.8 and 23.5; mass spectrum (APCI), m/z 225.1246 (M+H)+ (C11H17N2O3 requires 225.1239).

Workup

extractionextracted with two 80-mL portions of ethyl acetate
washThe combined organic solution was washed with one 80-mL portion of brine
dry with materialdried (MgSO4)
concentrationconcentrated under diminished pressure
customThe residue was purified by chromatography on a silica gel column (3×10 cm)
washElution with 1:1 hexanes-diethyl ether

Sources & evidence

ORD record: ord-899a370a81da498f89aca5492ebd54be
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952025B2

Reaction notes

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