Reaktion #5220

Reaktionsgleichung

2-iodo-3-quinolinecarboxaldehyde

NaBH4

→

3-hydroxymethyl-2-iodoquinoline

Ausbeute 84.4%

Lösungsmittel

CH3OH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrating the mixture to approximately one-half of its original volume, water (30 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   workup.WAITto stand at 5° C. overnight
4. 4
   FiltrationThe solids were filtered
5. 5
   Sonstigethe crude product (570 mg, 95%) was recrystallized from methanol

Vorschrift

To a stirred solution of 2-iodo-3-quinolinecarboxaldehyde (595 mg, 2.10 mmol) in 40 mL of CH3OH at 0° C. was added NaBH4 (86 mg, 2.31 mmol), and the mixture was stirred at 0° C. for 30 min. After concentrating the mixture to approximately one-half of its original volume, water (30 mL) was added and the mixture was allowed to stand at 5° C. overnight. The solids were filtered and the crude product (570 mg, 95%) was recrystallized from methanol to give 3-hydroxymethyl-2-iodoquinoline (505 mg, 84%) as colorless needles: mp 189°-190° C. 1H NMR (300 MHz, CDCl3) δ 8.19 (s, 1H), 7.99 (d, 1H, J=9 Hz), 7.87 (d, 1H, J=9 Hz), 7.68 (m, 1H), 7.58 (t, 1H, J=9 Hz), 5.45 (t, 1H, J=6 Hz), 4.66 (d, 2H, J=6 Hz); IR (nujol) 3350, 1580, 1320, 1125, 1060, 995, 755, 720, cm-1.

Quelle