Sodium Azide → Methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylate

HRID 655909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655909
Br[CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([O-:15])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[N-:22]=[N+:23]=[N-:24].[Na+].[CH2:26]1COCC1.CN(C=O)C>>[N:22]([CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([O:15][CH3:26])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N+:23]=[N-:24]

Komponenten

4

Edukt 3

HCID 33557Sodium AzideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 866180063-(Bromomethyl)-2-phenylquinoline-4-carboxylate

Produkt 1

HCID 57893572Methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylateAusbeute 99,7 %

Versuchsvorschrift

To a solution of 3-(bromomethyl)-2-phenylquinoline-4-carboxylate (2a) (2000 mg, 5.618 mmol) in THF/DMF (50 mL/10 mL) was added sodium azide (402 mg, 6.18 mmol) and the reaction mixture stirred at RT under N2 for 12 h. All solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine, dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography eluting with 10% ethyl acetate/hexane to give the title compound (1781 mg, 99.7%) as an off white solid. MS APCI, m/z=319 (M+1). LCMS: 2.34 min.

Aufarbeitung

  1. customAll solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography
  6. washeluting with 10% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ebad02c58a4449b5a30d3e7be0ffe794
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071621B2

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