5-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide → 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxide

HRID 1073944노트

반응식

HRID 1073944 반응식
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]2[C:21]3[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=[CH:25][C:20]=3[O:19][C:18]([CH3:29])([CH3:28])[CH2:17]2)=[N+:13]([O-:15])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:26]([C:23]1[CH:24]=[CH:25][C:20]2[O:19][C:18]([CH3:29])([CH3:28])[CH2:17][CH:16]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N+:13]=3[O-:15])[C:21]=2[CH:22]=1)#[N:27]

참가 물질

4

반응물 1

HCID 538667995-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide

생성물 1

HCID 540062792-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxide수율 31.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

0.21 g of 5-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide in 90 ml of methanol was hydrogenated over 10% palladium-on-carbon at room temperature and under atmospheric pressure for 30 minutes. The catalyst was removed by filtration and the filtrate was evaporated. The residue was chromatographed on silica gel using dichloromethane/methanol (19:1) for the elution to give 0.05 g of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxide in the form of an off-white solid of melting point 224° C. (from ethyl acetate).

후처리

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution

출처 및 근거

ORD 기록
ord-5fd2148a479a4abcac79e14bcb769fe6
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04971982

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