Water → HCID 21953491, compound

Participants

Reaction Steps

2-Iodobenzaldehyde prepared above (10.3 g, 44.4 mmol) was dissolved in 50 mL MeOH and 10 mL THF. After addition of H2NOH.HCl (10 mL H2O) and 6N KOH, an additional 50 mL THF, 30 mL H2O, and 30 mL MeOH were added. The product was recovered as a cloudy orange oil (9.46 g, 85.6%, 90% desired product). IR (film): 3256, 3057, 2872, 1564, 1466, 1435, 1013, 748. 1H-NMR (400 MHz, CDCl3): δ 7.92 (dd, 1H, J=7.8, 1.2, C4-H), 7.58 (dd, 1H, J=7.4, 1.8, C7-H), 7.34 (td, 1H, J=7.4, 1.2, C6-H), 7.00 (td, 1H, J=7.6, 1.8, C5-H), 5.5 (br s, 1H, C1-NHOH), 5.0 (br s, 1H, C1-NHOH), 4.13 (s, 2H, C1-H2). 13C-NMR (100 MHz, CDCl3): δ 139.5, 139.1, 131.0, 129.4, 128.3, 100.1, 62.0. EI-MS m/z (rel int): 249 (M+, 36), 217 ([M−NHOH]+, 100), 122 ([M−I]+, 30). CI-MS (NH3) m/z (rel int): 284 ([M+2NH3+H]+, 30), 267 ([M+NH4]+, 100), 250 ([M+H]+, 27).

Provenance & Evidence