Reaktion #57938

Reaktionsgleichung

4-nitro-anthranilic acid methyl ester

triethylamine

4-tert-butyl benzoyl chloride

→

2-(4-tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester

Ausbeute 60.0%

Lösungsmittel

CH2Cl2

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   Trocknendried over MgSO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe residue was purified by flash chromatography

Vorschrift

To a solution of 4-nitro-anthranilic acid methyl ester (1.500 g, 7.4 mmol) in CH2Cl2 (200 mL) was added triethylamine (8 mL) and 4-tert-butyl benzoyl chloride and the reaction was stirred overnight at rt. It was then poured into brine, extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 2-(4-tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester (1.841 g, 60%) as a yellow solid. mp=146.0-148.4° C.; mass spectrum (−ES, M−H) in/z 355. 1H NMR (400 MHz, DMSO-d6); δ 11.60 (bs, 1H), 9.35 (d, 1H), 8.20 (d, 1H), 8.02 (dd, 1H), 7.90 (d, 2H), 7.64 (d, 2H), 3.95 (s, 3H), 1.36 (s, 9H). Elemental analysis: Calcd. for C19H20N2O5: C, 64.04; H, 5.66; N, 7.86, Found: C, 64.04; H, 5.79; N, 7.76.

Quelle