Hantzsch ester → 2-Pyridin-2-yl-1,2,3,4-tetrahydroquinoline

HRID 589096

반응식

HRID 589096 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.C(C1CC(C(OCC)=O)=C(C)NC=1C)(OCC)=O.C1(C2C=CC3C(=CC=CC=3)N=2)C=CC=CC=1>C1C=CC=CC=1.P(O)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8]1

참가 물질

6

반응물 3

HCID 70849Hantzsch esterHCID 715452-PhenylquinolineHCID 6099112-(2-Pyridinyl)quinoline

생성물 1

HCID 904098222-Pyridin-2-yl-1,2,3,4-tetrahydroquinoline수율 94%

시약·촉매·용매 2

HCID 13282Phosphoric acid, diphenyl ester촉매HCID 241Benzene용매

반응 조건

온도
60 °C

실험 절차

A suspension of 2-pyridin-2-ylquinoline (0.767 g, 3.72 mmol), 1,4-dihydro-3,5-dicarbethoxy-2,6-dimethylpyridine (2.17 g, 8.55 mmol), and diphenyl hydrogen phosphate (0.0093 g, 0.037 mmol) in benzene (18.6 mL) was heated at 60° C. for 10 h. The reaction mixture was treated with 2-phenylquinoline (0.305 g, 1.49 mmol) and heated at 60° C. for 3 h. The reaction mixture was then concentrated to a crude solid. Purification by flash column chromatography (100% hexanes to 50% ethyl acetate/hexanes [the ethyl acetate contained 5% methanol]) gave the desired product (0.735 g, 94%) as a racemic mixture. LCMS calculated for C14H15N2 (M+H)+: m/z=211.1. found: 211.1.

후처리

  1. temperatureheated at 60° C. for 3 h
  2. concentrationThe reaction mixture was then concentrated to a crude solid
  3. customPurification by flash column chromatography (100% hexanes to 50% ethyl acetate/hexanes [the ethyl acetate

출처 및 근거

ORD 기록
ord-7a113bd58e384bfeb7125394694985eb
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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