3,5-Bis-trifluoromethyl-benzaldehyde oxime → 4-[3-[(E)-[3,5-bis(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]-2-hydroxybenzoic acid
Reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[OH:15].[F:17][C:18]([F:33])([F:32])[C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH:22]=[N:23][OH:24]>>[F:17][C:18]([F:32])([F:33])[C:19]1[CH:20]=[C:21](/[CH:22]=[N:23]/[O:24][CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:16])=[C:5]([OH:15])[CH:6]=2)[CH:25]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:27]=1Participants
3
Procedure
The title compound (0.115 g, 12%) was prepared as a white solid from 4-(3-bromo-propoxy)-2-hydroxy-benzoic acid methyl ester and 3,5-bis-trifluoromethyl-benzaldehyde oxime using a procedure similar to step 1 of example 12. mp=181.9-183.4° C.; mass spectrum −ESI, (M−H) m/z 450. 1H NMR (400 MHz, DMSO-d6); 613.60 (bs, 1H), 11.50 (bs, 1H), 8.48 (s, 1H), 8.23 (s, 2H), 8.13 (s, 1H), 7.66 (d, 1H), 6.47 (m, 2H), 4.33 (t, 2H), 4.12 (t, 2H), 2.12 (m, 2H). Elemental analysis: Calcd. for C19H15F6NO5: C, 50.56; H, 3.35; N, 3.1, Found: C, 50.25; H, 3.32; N, 2.93.
Sources & evidence
- ORD record
- ord-11794c11ad934cf7a0ae3c2b1be1aaa6
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420083B2
Reaction notes
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