ANTHRANILIC ACID, N-BOC-5-HYDROXY synthesis
- Product Name:ANTHRANILIC ACID, N-BOC-5-HYDROXY
- CAS Number:244765-00-2
- Molecular formula:C12H15NO5
- Molecular Weight:253.25
60-29-7
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$34.10/50g
24424-99-5
858 suppliers
$13.50/25G
394-31-0
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$7.00/5g
244765-00-2
50 suppliers
$16.00/250mg
Yield:244765-00-2 92.5%
Reaction Conditions:
with phosphoric acid;sodium carbonate in tetrahydrofuran;
Steps:
1.A A.
A. N-Boc-5-hydroxyanthranilic acid [1] 5-Hydroxyanthranilic acid (100 g, 0.65 mol) was transferred into a 5 liter 3-necked round bottom flask equipped with a mechanical stirrer. A solution of saturated sodium carbonate (1.5 liters) was added to the reaction flask with stirring. After carbon dioxide evolution had subsided, di-t-butyldicarbonate (156.8 g, 0.72 mol) in 1.5 liters of tetrahydrofuran (THF) was added to the reaction vessel which was stirred at a rate which insured complete mixing of the resulting biphasic mixture. The reaction mixture was stirred at room temperature for 24 hours at which time 1.0 liters of ethyl ether was added and the mixture transferred to a separatory funnel. The aqueous layer was extracted with an additional 1.0 liters of ethyl ether and brought to pH=3.0 with 2 M H3PO4. Product was extracted from the aqueous solution with ethyl acetate (3*1.0 liters). The combined organics were washed with a saturated NaCl solution, dried over Na2SO4, filtered and concentrated in vacuo to yield N-Boc-5-hydroxyanthranilic acid (153 g, 92.5% yield).
References:
US6171578,2001,B2
24424-99-5
858 suppliers
$13.50/25G
244765-00-2
50 suppliers
$16.00/250mg