4-(Benzyloxy)benzoic acid → HCID 18422092, compound

Participants

Reaction Steps

Using analogous procedures to those described in the last two paragraphs of the portion of Example 7 which is concerned with the preparation of starting materials, 4-benzyloxybenzoic acid was reacted with N-(3-amino-4-methylphenyl)quinoline-6-carboxamide to give N-[3-(4-benzyloxybenzamido)-4-methylphenyl]quinoline-6-carboxamide in 50% yield, m.p. 227-228° C.; NMR Spectrum: (DMSOd6) 2.21 (s, 3H), 5.2 (s, 2H), 7.12 (d, 2H), 7.25 (d, 1H), 7.39 (m, 5H), 7.61 (m, 2H), 7.86 (d, 1H), 8.52 (d, 1H), 8.62 (d, 1H), 8.99 (m, 1H), 9.76 (s, 1H), 10.47 (s, 1H); and that compound was hydrogenolysed to give the required starting material in 93% yield; NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 6.83 (d, 2H), 7.23 (d, 1H), 7.61 (m, 2H), 7.85 (m, 3H), 8.12 (d, 1H), 8.25 (d, 1H), 8.52 (d, 1H), 8.62 (s, 1H), 8.99 (d, 1H), 9.61 (s, 1H), 10.46 (s, 1H); Mass Spectrum: M−H− 396.

Provenance & Evidence