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

HRID 1043784

反応式

HRID 1043784 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4851d149901c4300830f4a00cd020306
出典データセット
uspto-grants-2013_10
特許番号
US08563549B2

関連ノート

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