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Nitric Acid → Methyl 2-amino-5-nitronicotinate

HRID 2079938
ノート
印刷プレビュー

反応式

HRID 2079938 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 13063488Methyl 2-amino-5-nitronicotinate収率 35%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8a9ec757a2742cbbfa77f9f6d3650ea
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932272B2

反応ノート

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