N-bromobutanimide → 5-Bromo-2-tert-butylpyridin-4-amine

HRID 921034ノート

反応式

HRID 921034 の反応式
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(#N)C>[Br:1][C:16]1[CH:15]=[N:14][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[CH:18][C:17]=1[NH2:19]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 8177532-(tert-Butyl)pyridin-4-amine

生成物 1

HCID 679958335-Bromo-2-tert-butylpyridin-4-amine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Procedure analogous to V. Canibano et al., Synthesis 2001, 14, 2175. 18.7 g (105 mmol) of N-bromosuccinimide are added in portions at 40° C. to a vigorously stirred, light-protected solution of 15.0 g (100 mmol) of 2-tertbutyl-4-aminopyridine [39919-69-2] in 500 ml of acetonitrile, and the mixture is stirred for a further 30 h. The solvent is removed in vacuo, the residue is taken up in 500 ml of dichloromethane, washed five times with 500 ml of water each time and once with 300 ml of sat. sodium chloride solution, the organic phase is dried over sodium sulfate, and the solvent is then removed in vacuo. The crude product is recrystallised from cyclohexane. Yield: 17.9 g (78 mmol), 78%. Purity: >95% according to 1H-NMR.

後処理

  1. customCanibano et al., Synthesis 2001, 14, 2175
  2. customThe solvent is removed in vacuo
  3. washwashed five times with 500 ml of water each time
  4. dry with materialonce with 300 ml of sat. sodium chloride solution, the organic phase is dried over sodium sulfate
  5. customthe solvent is then removed in vacuo
  6. customThe crude product is recrystallised from cyclohexane

出典と根拠

ORDレコード
ord-b754e70795634231ada8e1d6430e4e04
出典データセット
uspto-grants-2016_03
特許番号
US09273080B2

反応ノート

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