N-[(4-tert-butylphenyl)methylidene]hydroxylamine → 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[2-(trifluoromethyl)benzoyl]amino]benzoic acid

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Reaction Steps

The title compound (0.117 g, 64%) was prepared as a white solid from 4-(3-bromo-propoxy)-2-(2-trifluoromethyl-benzoylamino)-benzoic acid methyl ester and 4-tert-butyl-benzaldehyde oxime using a procedure similar to step 1 of example 6. mp=121.1-122.0° C.; mass spectrum API-ES, (M−H) m/z 541. 1H NMR (400 MHz, DMSO-d6); δ 13.40 (bs, 1H), 11.90 (bs, 1H), 8.28 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.88 (d, 1H), 7.80 (m, 3H), 7.50 (d, 2H), 7.39 (d, 2H), 6.82 (dd, 1H), 4.28 (t, 2H), 4.18 (t, 2H), 2.15 (m, 2H), 1.25 (s, 9H). Elemental analysis: Calcd. for C29H29F3N2O5: C, 62.2; H, 5.39; N, 5.16, Found: C, 63.8; H, 5.26; N, 5.04.

Provenance & Evidence