Réaction #432016

Équation de réaction

hydrochloric acid

N-methoxy-N-methyl anthranilic acid amide

n-BuLi

4-benzyloxy-bromobenzene

→

4'-benzyloxy-2-aminobenzophenone

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autreat -78° C.
2. 2
   Extractionthe mixture extracted with ethyl acetate (150 ml), ethyl acetate
3. 3
   Lavagewashed with water, brine
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   AutreRecrystallization from hexanes

Mode opératoire

To a mixture of N-methoxy-N-methyl anthranilic acid amide prepared as in Example 1(A)(2.00 g, 11.1 mmol) and 4-benzyloxy-bromobenzene (2.92 g, 11.1 mmol) in anhydrous tetrahydrofuran (65 ml) at -78° C. under nitrogen is added, with vigorous stirring, n-BuLi in hexanes (13.8 ml, 1.6M, 22.2 mmol) at 0.60 ml/min. After 20 min, aqueous hydrochloric acid is added (1N, 20 ml), the mixture extracted with ethyl acetate (150 ml), ethyl acetate washed with water, brine, dried over magnesium sulfate, and concentrated. Recrystallization from hexanes gave 4'-benzyloxy-2-aminobenzophenone as yellow crystals; yield: 2.35 g, (70%); m.p. 99°-101° C.

Source