Cyclohexanol → 3-Cyclohexyloxy-6,7-dimethoxy-quinoline

HRID 23337

반응식

HRID 23337 반응식
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.[CH:16]1(O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:16]1([O:1][C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=3)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

6

반응물 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 100587666,7-Dimethoxyquinolin-3-ol

생성물 1

HCID 99040183-Cyclohexyloxy-6,7-dimethoxy-quinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a THF solution (30 mL) at 0° C. is added 3-hydroxy-6,7-dimethoxyquinoline (0.237 g, 1.15 mmol), cyclohexanol (0.347 g, 3.46 mmol), Ph3P (0.908 g, 3.46 mmol). Diethylazodicarboxylate is added portionwise until the solution retained a deep red color (0.663 g, 3.81 mmol). After 4 hours the solution is concentrated and the residue chromatographed (50% EtOAc in hexanes). The product is recrystallized from isopropanol/hexanes as the HCl salt as a white solid (m.p. 229-232° C., dec.).

후처리

  1. concentrationAfter 4 hours the solution is concentrated
  2. customthe residue chromatographed (50% EtOAc in hexanes)
  3. customThe product is recrystallized from isopropanol/hexanes as the HCl salt as a white solid (m.p. 229-232° C., dec.)

출처 및 근거

ORD 기록
ord-08e2a2c1bd0947beb25af09a094e127e
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852712B2

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