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Oxidative Hydrolysis of N-Benzylisatin using peroxide; N-protected Anthranilic Acid

SyntheticPage 482
DOI: 10.1039/SP482
Submitted Feb 05, 2011, published Feb 10, 2011
Abir Kumar Pal (abirchem2@yahoo.com)


			Reaction Scheme: Oxidative Hydrolysis of <SPAN id=csm1297446122552 class=csm-chemical-name title=N-Benzylisatin grpid="1">N-Benzylisatin</SPAN> using peroxide

Chemicals Used

N-benzylisatin (see references)
NaOH (SDFCL)

H2O2 (Qualigen)

Procedure

N-benzylisatin (1.5g, 6.3 mmol) was dissolved in  NaOH solution (0.756g was dissolved in 15cmDM 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%)

Author's Comments

Higher batch size results higher yield and purity

Data

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).

(M+H): 228.20


Lead Reference

Nard C. Sumpter Chem. Rev., 1944, 34(3), pp 393-434,


 

Other References

Reference for N-benzylisatin preparation:
1. Synthesis, (10), 1731-1735: 2010.
2. Bioorganic & Medicinal Chemistry, 17(21), 7562-7571; 2009.
3. Organic Letters, 11(17), 3854-3857; 2009.
4. JOC, 74(10), 3990-3992; 2009.
 

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Keywords: amines, hydroxylation, oxidation

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