Benzaldehyde → Benzaldehyde-O-(3-carboxyphenyl)oxime

HRID 971176Notes

Reaction equation

HRID 971176 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:13]=[C:14]([O:18][NH2:19])[CH:15]=[CH:16][CH:17]=1)([OH:11])=[O:10]>>[C:9]([C:12]1[CH:13]=[C:14]([O:18][N:19]=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:16][CH:17]=1)([OH:11])=[O:10]

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 11480924O-(3-Carboxyphenyl)hydroxylamine

Product 1

HCID 72805614Benzaldehyde-O-(3-carboxyphenyl)oximeYield 58.1%

Procedure

Benzaldehyde (21.0 μL, 0.207 mmol) was subjected to the representative coupling procedure with 3 (31.8 mg, 0.208 mmol) as outlined above (method 2), yielding 3a as a white solid (29.0 mg, 58%). 1H-NMR (500 MHz, 1:1 CD3OD:d6-DMSO) δ 7.39-7.45 (m, 5H), 7.59-7.64 (m, 1H), 7.71-7.78 (m, 3H), 8.58 (s, 1H); 13C-NMR (125 MHz, d6-DMSO) δ 114.5, 118.8, 123.3, 127.7, 129.1, 129.3, 130.8, 131.1, 132.3, 153.3, 158.9, 166.9; MALDI-FTMS (DHB) 242.0812 m/z [MH]+, C14H12NO3 requires 242.0812. RP-HPLC: 98% pure.

Sources & evidence

ORD record
ord-445c82eddbf344c3984fd2e7ca5e490e
Source dataset
uspto-grants-2007_12
Patent number
US07312361B2

Reaction notes

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