Sodium Methoxide → 6-(2,6-Diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10](Cl)=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])C.[CH3:24][O-:25].[Na+]>>[CH3:1][O:3][C:4](=[O:23])[C:5]1[C:10]([O:25][CH3:24])=[CH:9][C:8]([C:12]2[C:13]([CH2:20][CH3:21])=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:18][CH3:19])=[N:7][C:6]=1[CH3:22]Participants
3
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester (165 mg, 0.5 mmol) and sodium methoxide (0.5 M in methanol, 4 mL, 2.0 mmol) is heated at 65° C. for 16 hours. The volatile material is removed in vacuo and the residue is partitioned between ethyl acetate (50 mL) and water (20 mL). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 mL). The combined organic extract is dried and concentrated in vacuo. The crude product is purified by PTLC (hexanes/ethyl acetate 4:1) to give 6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester. 1H NMR: (CDCl3) 7.26 (m, 2H), 7.13 (d, 2H), 3.98 (s, 3H), 3.85 (s, 3H), 2.56 (s, 3H), 2.32 (m, 4H), 1.04 (t, 6H).
Workup
- customThe volatile material is removed in vacuo
- customthe residue is partitioned between ethyl acetate (50 mL) and water (20 mL)
- customThe organic layer is separated
- extractionthe aqueous layer is extracted with ethyl acetate (2×20 mL)
- extractionThe combined organic extract
- customis dried
- concentrationconcentrated in vacuo
- customThe crude product is purified by PTLC (hexanes/ethyl acetate 4:1)
Sources & evidence
- ORD record
- ord-d3d1dfafbd4d4c64aa477a0fde0f8df3
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07342115B2
Reaction notes
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