Reaktion #57952

Reaktionsgleichung

4-amino-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

sodium nitrite

→

4-hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

Ausbeute 83.0%

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was produced
2. 2
   SonstigeThe crude material was purified by flash chromatography through silica gel

Vorschrift

This compound was produced using similar methods as those used in Step 3, example 27, starting with 4-amino-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.80 g, 5.08 mmol), trifluoroacetic acid (30 mL) and sodium nitrite (0.42 g, 6.15 mmol in 10 mL of water). The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 20/80) to give 4-hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.49 g, 83%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6); δ 11.98 (s, 1H), 10.62 (s, 1H), 8.21 (d, 1H), 8.06 (d, 2H), 7.90 (d, 1H), 7.61 (d, 2H), 6.61 (dd, 1H), 3.84 (s, 3H).

Quelle