Acetic Acid → Benzoic acid, 2-[(4-pyridinylmethyl)amino]-, methyl ester

HRID 1279487ノート

反応式

HRID 1279487 の反応式
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.[C:13]([O:22][CH3:23])(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH2:16].C([BH3-])#N.[Na+]>CO>[N:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:16][C:15]2[C:14](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([O:22][CH3:23])=[O:21])=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8635Methyl AnthranilateHCID 133894-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydride2 回

生成物 1

HCID 10879301Benzoic acid, 2-[(4-pyridinylmethyl)amino]-, methyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3 mL Acetic acid and 8.6 g 4-pyridinecarbaldehyde are added to a solution of 7.5 g methyl anthranilate in 300 mL methanol. The mixture is stirred for 12 hours under nitrogen atmosphere at room temperature. 5.7 g Sodium cyanotrihydridoborate (85%) is added and the mixture is stirred for 3 hours at room temperature. Additional 1.14 g sodium cyanotrihydridoborate (85%) is added and the mixture is stirred for 12 hours at room temperature. The solvent is evaporated and the residue dissolved in ethyl acetate and washed with saturated NaHCO3 solution and saturated sodium chloride solution. The organic extract is concentrated and purified with hexane/ethyl acetate (1:1) on silica gel to yield methyl N-(4-pyridylmethyl)-anthranilate with m.p. 86° C.

後処理

  1. stirringthe mixture is stirred for 3 hours at room temperature
  2. stirringthe mixture is stirred for 12 hours at room temperature
  3. customThe solvent is evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with saturated NaHCO3 solution and saturated sodium chloride solution
  6. extractionThe organic extract
  7. concentrationis concentrated
  8. custompurified with hexane/ethyl acetate (1:1) on silica gel

出典と根拠

ORDレコード
ord-bf59e6b411804a558a433c17c8f5a3ab
出典データセット
uspto-grants-2002_09
特許番号
US06448277B2

反応ノート

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