Nicotinic Acid → 3-(Azidomethyl)pyridine

HRID 1866852노트

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HRID 1866852 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 457912673-(Azidomethyl)pyridine수율 84.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-38018a0861d34872905b35ddd721e662
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629467B2

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