Sodium borohydride → (2-Iodoquinolin-3-yl)methanol

HRID 5124

Reaktionsgleichung

Reaktionsgleichung von HRID 5124
[I:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[BH4-].[Na+]>CO>[OH:13][CH2:12][C:11]1[C:2]([I:1])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 109897002-Iodoquinoline-3-carbaldehyde

Produkt 1

HCID 13527196(2-Iodoquinolin-3-yl)methanolAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationAfter concentrating the mixture to approximately one-half of its original volume, water (30 mL)
  2. additionwas added
  3. waitto stand at 5° C. overnight
  4. filtrationThe solids were filtered
  5. customthe crude product (570 mg, 95%) was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-12269c99e5404be9b05d3835e65be89c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243050

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