Reaktion #161284

Reaktionsgleichung

sodium cyanoborohydride

acetic acid

formaldehyde

N-(3-amino-4-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide

formaldehyde

→

N-(3-dimethylamino-4-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide

Ausbeute 17.0%

Lösungsmittel

ether

CH2Cl2

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 4.7 h
2. 2
   Waschenwashed with water (25 mL) and brine (25 mL)
3. 3
   Trocknendried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe resulting red-brown foam was purified by preparative HPLC

Vorschrift

To a suspension of N-(3-amino-4-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (271) (600 mg, 1.8 mmol) in CH2Cl2 (15 mL) and methanol (5 mL) were added acetic acid (250 μL) and formaldehyde (268 μL, 3.6 mmol, 37 wt % in water). After 10 min, sodium cyanoborohydride (407 mg, 6.5 mmol) was added in one portion. Additional formaldehyde (135 μL, 1.8 mmol, 37 wt % in water) was added at 1.5 and 4.2 h. After 4.7 h, the mixture was diluted with ether (40 mL), washed with water (25 mL) and brine (25 mL), dried (Na2SO4), filtered, and concentrated. The resulting red-brown foam was purified by preparative HPLC to afford N-(3-dimethylamino-4-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (485) (108 mg, 17%). 1H NMR (300 MHz, CDCl3) δ 13.13 (br s, 1H), 12.78 (s, 1H), 8.91 (br s, 1H), 8.42 (br s, 1H), 8.37 (d, J=8.1 Hz, 1H), 7.72-7.58 (m, 2H), 7.47-7.31 (m, 3H), 3.34 (s, 6H), 1.46 (s, 9H); HPLC ret. time 2.15 min, 10-100% CH3CN, 5 min run; ESI-MS 364.3 m/z (MH+).

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