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Nitric Acid → Methyl 2-amino-5-nitronicotinate

HRID 2079938
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HRID 2079938 반응식
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[NH2:10].C(=O)(O)[O-].[Na+].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=[N:6][C:5]=1[NH2:10]
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참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 516892Sodium Bicarbonate

생성물 1

HCID 13063488Methyl 2-amino-5-nitronicotinate수율 35%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
0 °C

실험 절차

2-Amino-nicotinic acid methyl ester (1.00 g, 6.57 mmol) described in Preparation Example A-2 was dissolved at 0° C. in a mixed solution of nitric acid (0.7 mL) and sulfuric acid (2.6 mL), which was stirred at 0° C. for 40 minute and at room temperature for 19 hours, then, further stirred at 70° C. for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0° C., which was extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. Methanol was added to the residue, the precipitated solid was filtered to obtain the title compound (459 mg, 2.33 mmol, 35%) as a white solid.

후처리

  1. stirringfurther stirred at 70° C. for 4 hours
  2. extractionwhich was extracted with ethyl acetate and tetrahydrofuran
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. additionMethanol was added to the residue
  7. filtrationthe precipitated solid was filtered

출처 및 근거

ORD 기록
ord-e8a9ec757a2742cbbfa77f9f6d3650ea
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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