Benzaldehyde → HCID 66718186, compound

HRID 1514747Notes

Reaction equation

HRID 1514747 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC[O-].[Na+].Cl>C(O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:6]([C:4]([OH:3])=[O:5])=[C:10](/[CH:11]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:9][N:8]=2)=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66599060HCID 66599060, compound

Product 1

HCID 66718186HCID 66718186, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (1.05 g, 4.2 mmol) and benzaldehyde (0.42 mL, 4.2 mmol) in ethanol (6 mL) was added sodium ethylate (1.5 g, 4.6 mmol) and the reaction mixture was stirred at reflux for 30 min. Aqueous hydrochloric acid (1 M, 5 mL) was added and stirring was continued for 15 min. The precipitate was filtered and dried to afford the title compound (1.2 g, 85%) as an off-white solid. MS: m/e=309.3 [M−H]−.

Workup

  1. temperatureat reflux for 30 min
  2. stirringstirring
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-d69d2d055e2a4f9caa051ca1955814a1
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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