ChemicalBook CAS DataBase List ethyl 2-amino-3-nitro-benzoate

ethyl 2-amino-3-nitro-benzoate synthesis

9synthesis methods

Product Name:ethyl 2-amino-3-nitro-benzoate
CAS Number:61063-11-4
Molecular formula:C9H10N2O4
Molecular Weight:210.19

Ethyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate

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61063-11-4
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Yield:61063-11-4 99%

Reaction Conditions:

with acetyl chloride in methanol;ethyl acetate at 0 - 20; for 64 h;

Steps:

7.I

Example 7:; 2-Ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazoIe-4-carboxyIic acid (candesartan) (If); Step I: 2-Amino-3-nitro-benzoic acid ethyl ester (VII); HCl IN (10 niL) [a solution of HCl IN (25 mL) was prepared by dropwise acetyl chloride (1.78 mL) in MeOH (3.22 mL) and diluting with AcOEt (20 mL)] was slowly added dropwise to ethyl 2-[(fert-butoxycarbonyl)amino]-3-n_.itrobenzoate (VI) (1 g, 0.00323 mol), under N₂ atmosphere, at 0⁰C. The solution was kept at 0°C for 5', than stirred at room temperature for 64 hrs (TLC monitoring: cyclohexane/AcOEt 2:1). A saturated solution of NaHCO₃ was added to the mixture and the mixture was extracted several times with AcOEt. The organic phase was dried over Na₂SO₄ and concentrated under reduced pressure to give the compound (VII) (0.67 g) as a yellow solid, m.p. 108°C. Yield: 99%.[¹H] NMR (400 MHz, CDCl₃, δ): 1.40 (t, J=7.1Hz, 3H, OCH₂CH₅), 4.37 (q, J=7.1ηz, 2H, OCH₂CH₃), 6.65 (dd, J=8.0Hz, 8.0Hz, IH) 8.25 (dd, J=7.6Hz, 1.2Hz, IH) 8.37 (dd, J=7.6Hz, 1.2Hz, IH) (aromatic protons), 8.46 (bs, 2H, NH₂).