Lithium Carbonate → 8,9-dihydro-3-nitro-5H-benzocyclohepten-5-one

HRID 262528

반응식

HRID 262528 반응식
C(=O)([O-])[O-].[Li+].[Li+].[Br-].[Li+].Br[CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:12]=2[C:11]1=[O:24]>CN(C)C=O>[N+:21]([C:19]1[CH:18]=[CH:17][C:13]2[CH2:14][CH2:15][CH:16]=[CH:10][C:11](=[O:24])[C:12]=2[CH:20]=1)([O-:23])=[O:22]

참가 물질

5

반응물 3

HCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 542772843-nitro-6-bromo-6,7,8,9-tetrahydro [5H] benzocycloheptene-5-one

생성물 1

HCID 200947328,9-dihydro-3-nitro-5H-benzocyclohepten-5-one수율 73.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 548 g of lithium carbonate, 548 g of lithium bromide and 5.480 liters of dimethylformamide was heated to 100° C. and 548 g of the product of Step A was added thereto over 5 minutes. The mixture was held at 100° C. for 45 minutes and was then poured into 25 liters of a water-ice-mixture. The mixture was vacuum filtered and the insolubles were extracted 8 times with one liter of methylene chloride. The organic phase was washed with water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The red crystalline mass was empasted successively 3 times with 400 ml of ether, once with 400 ml of ethanol and once with 400 ml of ether and was dried at 40° C. to obtain 286.7 g of 3-nitro-8,9-dihydro [5H] benzocycloheptene-5-one in the form of red-orange crystals melting at 128° C.

후처리

  1. waitThe mixture was held at 100° C. for 45 minutes
  2. filtrationfiltered
  3. extractionthe insolubles were extracted 8 times with one liter of methylene chloride
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. dry with materialonce with 400 ml of ethanol and once with 400 ml of ether and was dried at 40° C.

출처 및 근거

ORD 기록
ord-aa31fa707f724a968e47455966e2466a
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04154852

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