Hippuric Acid → (Z)-methyl 2-methoxy-6-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)benzoate

HRID 1476829Notes

Reaction equation

[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:4]=1[C:5]([O:7][CH3:8])=[O:6])=O.[C:15]([NH:23][CH2:24][C:25]([OH:27])=[O:26])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC([O-])=O.[Na+]>C(OC(=O)C)(=O)C>[CH3:14][O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:3](/[CH:1]=[C:24]2\[N:23]=[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:27][C:25]\2=[O:26])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-formyl-6-methoxybenzoate (1.6 g, 8.24 mmol) in acetic anhydride (10 mL) was added 2-benzamidoacetic acid (1.77 g, 9.88 mmol) and NaOAc (810 mg, 9.88 mmol). The mixture was heated at 100° C. in a microwave reactor. The reactant mixture was partitioned between EtOAc (30 mL) and H2O (50 mL). The organic layer was washed with saturated aqueous Na2CO3 (5×30 mL), dried over Na2SO4, and concentrated to give the title compound (7 g). ESI-MS m/z [M+H]+ 338.1.

Workup

customThe reactant mixture was partitioned between EtOAc (30 mL) and H2O (50 mL)
washThe organic layer was washed with saturated aqueous Na2CO3 (5×30 mL)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-d48afbf6e13d43608fd2694ce1d3328a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402841B2

Reaction notes

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