Toluene → 2-Amino-6-(2-cyanoethyl)-nicotinic acid methyl ester

HRID 2079950ノート

反応式

HRID 2079950 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[N:6][C:5]=1[NH2:12].[C-:14]#[N:15].C([Al+]CC)C.C1(C)C=CC=CC=1.[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:14]#[N:15])=[N:6][C:5]=1[NH2:12]

参加物

6

反応物 4

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 16686413Diethyl aluminum cyanideHCID 583190542-Amino-6-vinyl-nicotinic acid methyl ester

生成物 1

HCID 583879902-Amino-6-(2-cyanoethyl)-nicotinic acid methyl ester収率 21%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-amino-6-vinyl-nicotinic acid methyl ester (760 mg, 4.26 mmol) in tetrahydrofuran (76 mL) was added a solution of diethyl aluminum cyanide in toluene (12.8 mL, 12.8 mmol) dropwise under sodium chloride—an ice bath cooling, at an internal temperature of −5° C. or below, then, the solution was gradually allowed to room temperature and stirred overnight. The reaction solution was partitioned into an aqueous solution of saturated ammonium chloride and ethyl acetate. This organic layer was separated, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography, and the title compound (180 mg, 0.878 mmol, 21%) was obtained as a yellow oil.

後処理

  1. temperaturecooling, at an internal temperature of −5° C. or below
  2. customwas gradually allowed to room temperature
  3. customThe reaction solution was partitioned into an aqueous solution of saturated ammonium chloride and ethyl acetate
  4. customThis organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1fad45fe537746ec9e4f9f66498ed0a5
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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