Benzaldehyde → HCID 66718302, compound

HRID 1514725Notes

Reaction equation

HRID 1514725 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC[O-].[Na+].Cl>C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:7]1[C:6]([C:4]([OH:3])=[O:5])=[C:10](/[CH:11]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:9][N:8]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 22309063HCID 22309063, compound

Product 1

HCID 66718302HCID 66718302, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-3-pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester (3.0 g, 13 mmol) and benzaldehyde (1.32 mL, 13 mmol) in ethanol (20 mL) was added sodium ethylate (0.97 g, 14 mmol) and the reaction mixture was stirred at reflux for 40 min. Aqueous hydrochloric acid (1 M, 14 mL) was added and stirring was continued for 15 min. The precipitate was filtered and dried to afford the title compound (2.3 g, 61%) as an off-white solid. MS: m/e=290.9 [M−H]−.

Workup

  1. temperatureat reflux for 40 min
  2. stirringstirring
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-1d92b7294d2a4c45be40e0404742633a
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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