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2,6-Pyridinedicarboxylic acid → N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]acetamide

HRID 2268529
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HRID 2268529 반응식
C[O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16]C)=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH2:7]2.N1C(C(O)=O)=CC=CC=1C(O)=O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C.O.C(OCC)(=O)C>[CH3:13][O:12][C:11]1[C:3](=[O:2])[C:4]2[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH2:7][C:8]=2[C:9](=[O:16])[C:10]=1[O:14][CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348615N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]acetamide

생성물 1

HCID 18348613N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]acetamide수율 76.3%

시약·촉매·용매 3

HCID 962Water용매2회
HCID 6342Acetonitrile용매2회
HCID 8857Ethyl Acetate용매2회

실험 절차

To a mixture of N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]acetamide (700 mg), 2,6-pyridinedicarboxylic acid (857 mg), acetonitrile (7.0 ml), ethyl acetate (7.0 ml), and water (7.0 ml) was dropwise added a solution of CAN (3.75 g) in acetonitrile (3.5 ml) and water (3.5 ml) with cooling with ice. After being stirred for 15 min, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate) and then with recrystallization from hexane-ethyl acetate) to yield the entitled compound (495 mg) as crystals.

후처리

  1. temperaturewith cooling with ice
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customwith recrystallization from hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-1fbbb0fbb3e34e8c80f12d3205c5e1f5
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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