Benzaldehyde → Benzaldehyde-O-(2-carboxyphenyl)oxime
Reaction equation
C(=O)[C:2]1[CH:7]=[CH:6]C=[CH:4][CH:3]=1.C(O[C:12](=[N:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([OH:24])=[O:23])[CH3:13])C>>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][N:14]=[CH:12][C:13]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)([OH:24])=[O:23]Participants
3
Procedure
70% HClO4 (14.0 μL, 0.163 mmol), benzaldehyde (18.0 mL, 0.177 mmol), and 20 (39.0 mg, 0.175 mmol) were subjected to the representative coupling procedure as outlined above (method 3), yielding 2a as a white solid (26.1 mg, 62%). 1H-NMR (500 MHz, d6-Acetone) δ 7.15 (dt, J=0.9, 7.8 Hz, 1H), 7.48-7.55 (m, 3H), 7.59 (dt, J=1.8, 7.8 Hz, 1H), 7.71 (d, J=8.2 Hz, 1H), 7.83-7.89 (m, 3H), 8.66 (s, 1H), 10.8-11.5 (broad s, 1H); 13C-NMR (125 MHz, d6-DMSO) δ 115.7, 119.7, 122.1, 127.8, 129.0, 130.8, 130.9, 131.1, 133.1, 153.4, 157.7, 166.8; MALDI-FTMS (DHB) 242.0811 m/z [MH]+, C14H12NO3 requires 242.0812. RP-HPLC: >99% pure.
Sources & evidence
- ORD record
- ord-5254e110cd1246f5b3a5b12e429d7878
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312361B2
Reaction notes
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