Triphenylphosphine → 3-Nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline

HRID 1043784

Reaction equation

HRID 1043784 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[CH:5]2.[N:15]1([CH2:20][CH2:21]O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N+:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([O:1][CH2:21][CH2:20][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:11][CH:10]=2)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 595075803-Nitroquinolin-6-ol

Product 1

HCID 595075993-Nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinolineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-3-nitroquinoline (148 mg, 0.78 mmol) was dissolved in THF (18 mL). 2-(Pyrrolidin-1-yl)ethanol (0.091 mL, 0.78 mmol) and triphenylphosphine (306 mg, 1.17 mmol) were added. Lastly, diethyl azodicarboxylate (0.184 mL, 1.17 mmol) was added and the reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was then concentrated in vacuo and the residue was purified by flash chromatography (SiO2) to yield 134 mg (60%) of 3-nitro-6-(2-(pyrrolidin-1-yl)ethoxy)quinoline. LC/MS (m/z): 288.1 (MH+), Rt 1.80 minutes.

Workup

  1. concentrationThe solvent was then concentrated in vacuo
  2. customthe residue was purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-4851d149901c4300830f4a00cd020306
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Linked notes

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