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

HRID 1043784

반응식

HRID 1043784 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4851d149901c4300830f4a00cd020306
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563549B2

연결된 노트

불러오는 중…