Hydrazine hydrate (1:1) → 4-Hydroxymethyl benzophenone hydrazone

Participants

Reaction Steps

4-Bromomethyl benzophenone (2) was prepared as described in Reference Example 1. 4-Bromomethyl benzophenone (2) was converted into 4-Hydroxylmethyl benzophenone (3) as described in Reference Example 2. To solution of 3 (2.5 g, 12 mmol) in ethanol (20 ml) was added hydrazine hydrate (2.9 g 59 mmol). The mixture was heated to reflux for 24 h. then concentrated in vacuo. The residue was portioned between DCM and water and the organic layer collected and concentrated to yield 4 (2.6 g, 98%) a mixture of cis and trans isomers and as a yellow semi solid; δH (CDCl3) 2.84, 3.09 (2×bs, 1H, OH), 4.51, 4.61 (2×s, 2H, CH2OH), 5.32 (bs, 2H, NNH2), 7.13-7.17 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.30-7.43 (m, 5H, 2-, 2′-, 4′-, 6-, 6′-H) ppm; δC (CDCl3) 64.4, 64.6 (2×CH2OH), 126.4, 126.6, 127.7, 128.0, 128.1, 128.6, 128.8, 128.9, 129.3 (Ar—C), 131.8, 132.7 (2×1′-C), 137.5, 138.2 (2×1-C), 141.0, 141.8 (2×4′-C), 149.2 (C═N) ppm; νmax (thin film) 3384, 2870, 1583, 1444, 1412, 1015 cm−1; found (ES) 227.1180, C14H15N2O requires 227.1179.

Provenance & Evidence