Nicotinic Acid → 3-(Azidomethyl)pyridine

HRID 1866852ノート

反応式

HRID 1866852 の反応式
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C1(P([N:24]=[N+:25]=[N-:26])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:1]([N:24]=[N+:25]=[N-:26])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

参加物

6

反応物 3

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

生成物 1

HCID 457912673-(Azidomethyl)pyridine収率 84.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of nicotinic acid (1.23 g, 10.0 mmol) in DMF (15 mL) was added diphenylphosphoryl azide (2.60 mL, 12.0 mmol) followed by triethylamine (1.67 mL, 12.0 mmol). The mixture was stirred at room temperature for 2.5 h and diluted with water (50 mL). The mixture was extracted three times with EtOAc and the combined organic extracts were washed three times with water, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; hexane/EtOAc 7:3) provided I-3a as a white solid (1.13 g).

後処理

  1. extractionThe mixture was extracted three times with EtOAc
  2. washthe combined organic extracts were washed three times with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-38018a0861d34872905b35ddd721e662
出典データセット
uspto-grants-2009_12
特許番号
US07629467B2

反応ノート

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