Ethanol → Ethyl 6-Aminonicotinate

HRID 8945

反応式

HRID 8945 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][CH2:12]O>S(=O)(=O)(O)O>[CH2:11]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[N:3][CH:4]=1)[CH3:12]

参加物

4

反応物 2

HCID 702EthanolHCID 184966-Aminonicotinic acid

生成物 1

HCID 235927Ethyl 6-Aminonicotinate収率 92%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

A solution of 6-aminonicotinic acid (2.0 g, 14.4 mmol) in anhydrous EtOH (70 mL) and concentrated sulfuric acid (14 mL) was heated to reflux for 16 h. The solution was concentrated under reduced pressure, neutralized with saturated aqueous Na2CO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried (MgSO4), filtered and concentrated to give 6-aminonicotinic acid ethyl ester (2.18 g, 92%) as a white powder. 1H NMR (CDCl3) δ 1.37 (t, 3H, J=6.0 Hz), 4.34 (q, 2H, J=7.0 Hz), 4.89 (br s, 2H (NH2)), 6.46 (d, 1H, J=7.5 Hz), 8.02 (d, 1H, J=7.5 Hz), 8.73 (s, 1H).

後処理

  1. temperatureto reflux for 16 h
  2. concentrationThe solution was concentrated under reduced pressure
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f9221e72fbe144d09bdbb0a053ea0eea
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

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