Sodium Azide → 4-Azido-5-chloropyridine-3-carbaldehyde

HRID 626705ノート

反応式

HRID 626705 の反応式
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10])=[N+:12]=[N-:13]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 595965804,5-Dichloropyridine-3-carbaldehyde

生成物 1

HCID 866970494-Azido-5-chloropyridine-3-carbaldehyde収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4,5-dichloropyridine-3-carbaldehyde (6.78 g, 38.5 mmol) and sodium azide (2.62 g, 40.4 mmol) in DMF (25 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (250 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane) to afford the title compound as a yellow solid (6.7 g, 96% yield). 1H NMR (400 MHz, CDCl3): δ 10.36 (s, 1H), 8.84 (s, 1H), 8.65 (s, 1H).

後処理

  1. customThe reaction mixture was quenched with brine (250 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in pentane)

出典と根拠

ORDレコード
ord-6bfcfd0dc6364ef3a2a4de86f0e0f2bc
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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