N-benzylisatin (see references)NaOH (SDFCL)
N-benzylisatin (1.5g, 6.3 mmol) was dissolved in NaOH solution (0.756g was dissolved in 15cm3 DM water). Clear orange color solution was observed. The reaction mass was cooled to 15 to 20 °C. H2O2 (4.6 cm3, 50% w/w) was added dropwise (exothermic reaction). The reaction mass was heated to 50 to 60 °C and was stirred at that temperature for 2-3 h. The reaction was monitored by TLC(25% EA/ Hexane, 0.6 Rf of N-benzylisatin). After cooling to RT, the mixture was acidified with HCl (2N) up to pH 2~3 to give an off-white solid material which was filtered via Buchner funnel, washed with water (10 cm3) and the material dried under vacuum for 3-4 h. Yield: 1.1g (78%)
1H NMR (CDCl3, 400MHz): δ 12.0 (broad, 1H), δ7.90 (d, 1H), δ 7.56 (dd, 1H), δ 7.4 (dd, 2H), δ 7.31 (d, 2H), δ 7.25 (m, 1H), δ 6.81 (d, 1H), δ 6.65 (m, 1H), δ 4.3 (s, 2H).
Nard C. Sumpter Chem. Rev., 1944, 34(3), pp 393-434,
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