Water → HCID 59404399, compound

HRID 1873667Notes

Reaction equation

HRID 1873667 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][CH2:8][N:7]3[CH:6]=1)=[O:4].[N-:17]=[N+:18]=[N-:19].[Na+].O.C(OCC)(=O)C>CN(C=O)C>[N:17]([CH2:2][C:3]([C:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][CH2:8][N:7]3[CH:6]=1)=[O:4])=[N+:18]=[N-:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 59404402HCID 59404402, compound

Product 1

HCID 59404399HCID 59404399, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-ethanone (5.04 g, 21.6 mmol) and sodium azide (1.47 g, 22.7 mmol) in DMF (20 mL) was shaken for 16 h at room temperature. Water (200 mL) and ethyl acetate (200 mL) were added. The ethyl acetate layer was separated and washed twice with water (200 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (SiO2, neat DCM), to yield 2-azido-1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-ethanone as an off-white solid (4.70 g, 90%). M.p.=92-93° C.; 1H NMR (400 MHz, CDCl3) δ: 7.99 (d, J=8.0 Hz, 1H), 7.75 (s, 1H), 7.23 (m, 1H), 7.04 (d, J=7.6 Hz, 1H), 4.35 (s, 2H), 4.21 (t, J=5.6 Hz, 2H), 3.01 (t, J=6.4 Hz, 2H), 2.27 (m, 2H). LCMS: m/e 241.07 [M+H].

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed twice with water (200 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (SiO2, neat DCM)

Sources & evidence

ORD record
ord-a21284e9d27c41389bc8a4b72a9d928d
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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