N-[(4-tert-butylphenyl)methylidene]hydroxylamine → 4-[2-(4-Tert-butyl-benzylideneaminooxy)-ethoxy]-2-hydroxy-benzoic acid
Reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12]Br)=[CH:6][C:5]=1[OH:14].[C:16]([C:20]1[CH:28]=[CH:27][C:23]([CH:24]=[N:25][OH:26])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>>[C:16]([C:20]1[CH:28]=[CH:27][C:23]([CH:24]=[N:25][O:26][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:15])=[C:5]([OH:14])[CH:6]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]Participants
3
Procedure
The title compound was prepared as a white solid (3.056 g, 76%) from 4-(2-bromo-ethoxy)-2-hydroxy-benzoic acid methyl ester and 4-tert-butyl-benzaldehyde oxime using a procedure similar to that of step 1 of example 6. mp=161.4-162.7° C.; mass spectrum (+APCI, M+H) m/z 358. 1H NMR (400 MHz, DMSO-d6); δ 13.60 (bs, 1H), 11.50 (bs, 1H), 8.24 (s, 1H), 7.68 (d, 1H), 7.54 (d, 2H), 7.42 (d, 2H), 6.52 (m, 2H), 4.40 (t, 2H), 4.29 (t, 2H), 1.38 (s, 9H). Elemental analysis: Calcd. for C20H23NO5: C, 67.21; H, 6.49; N, 3.92, Found: C, 66.86; H, 6.42; N, 3.88.
Sources & evidence
- ORD record
- ord-aa8bb92f6e114e2b8ca9bfc5142fa9cd
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420083B2
Reaction notes
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