Phenol → 6-Methoxy-7-methyl-1-phenoxyisoquinoline

HRID 1366753노트

반응식

HRID 1366753 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+].[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:14][O:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[CH3:12])[C:2]([O:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:3][CH:4]=[CH:5]2

참가 물질

6

반응물 4

HCID 996PhenolHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 537828801-Chloro-6-methoxy-7-methylisoquinoline

생성물 1

HCID 669417846-Methoxy-7-methyl-1-phenoxyisoquinoline수율 19.6%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A mixture of 1-chloro-6-methoxy-7-methyl-isoquinoline (9 g, 43.48 mol), phenol (16.3 g), potassium hydroxide (9.45 g) and xylene (100 ml) was refluxed for 4 days. The reaction mixture was poured out into aqueous sodium hydroxide (4 M) and the xylene layer separated. The aqueous layer was extracted twice with toluene. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give a residue. The residue was purified by flash chromatography using dichloromethane gave 6-methoxy-7-methyl-1-phenoxyisoquinoline (9 g, 33.96 mmol).

후처리

  1. temperaturewas refluxed for 4 days
  2. customthe xylene layer separated
  3. extractionThe aqueous layer was extracted twice with toluene
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-f69c57d012bd4562b8f92e58c39a4652
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893088B2

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