Methyl 6-methylnicotinate → HCID 46872516, compound

HRID 1942272Notes

Reaction equation

HRID 1942272 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]=1[CH:24]=O>C(OC(=O)C)(=O)C.C(O)(=O)C.O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2](/[CH:1]=[CH:24]/[C:14]2[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:16][O:17][C:13]=2[CH3:12])=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 231548Methyl 6-methylnicotinateHCID 27761445-Methyl-3-phenylisoxazole-4-carboxaldehyde

Product 1

HCID 46872516HCID 46872516, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 6-methylnicotinate (800 mg, 5.29 mmol) in acetic anhydride (2.5 mL) and acetic acid (0.5 mL) was added 5-methyl-3-phenyl-4-isoxazolecarbaldehyde (1.0 g, 5.34 mmol) and the reaction mixture warmed to 120° C. After 8 days at this temperature, the reaction mixture was cooled to room temperature then diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, then dried, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1) to give the title compound (920 mg, 54%) as an off white solid. MS: m/e=321.0 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-a74731e22bee4da588d68e5535fc7c16
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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