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

HRID 1822064Notes

Reaction equation

HRID 1822064 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

HCID 57893572Methyl 3-(azidomethyl)-2-phenylquinoline-4-carboxylateYield 99.7%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e3d68ca60db64423811cf2827957de41
Source dataset
uspto-grants-2009_10
Patent number
US07608628B2

Reaction notes

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