4-Acetylbenzoic Acid → 4-{3E-[5-(3,5Dimethyl-isoxazol-4-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzoic acid

HRID 10642Notes

Reaction equation

HRID 10642 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:17][CH3:18])=[CH:9][C:10]([O:15][CH3:16])=[C:11]([CH:14]=2)[CH:12]=O)=[C:5]([CH3:19])[O:4][N:3]=1.[C:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)(=[O:22])[CH3:21]>>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:17][CH3:18])=[CH:9][C:10]([O:15][CH3:16])=[C:11](/[CH:12]=[CH:21]/[C:20]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)=[O:22])[CH:14]=2)=[C:5]([CH3:19])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 114704-Acetylbenzoic AcidHCID 219809665-(3,5-Dimethyl-isoxazol-4-yl)2,4-dimethoxy-benzaldehyde

Product 1

HCID 210416294-{3E-[5-(3,5Dimethyl-isoxazol-4-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzoic acidYield 7%

Procedure

The title compound was prepared by condensing 5-(3,5-dimethyl-isoxazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-33A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp>260° C., 7% yield. 1H-NMR (DMSO-d6) δ 8.15 (d, J=8 Hz, 2H), 8.04 (d, J=16 Hz, 1H), 8.02 (d, J=8 Hz, 2H), 7.89 (s, 1H), 7.81 (d, J=16 Hz, 1H), 6.79 (s, 1H), 4.00 (s, 3H), 3.97 (s, 3H), 2.23 (s, 3H) 2.05 (s, 3H) MS m/z=407 ([M]+, 60%), 376 (100%). HMRS (EI) calcd. for C23H21NO6: 407.1369; found: 407.1375.

Sources & evidence

ORD record
ord-bf5538abf09f4116b115afb71cb81295
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

Loading…