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

HRID 262528

反応式

HRID 262528 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-aa31fa707f724a968e47455966e2466a
出典データセット
uspto-grants-1979_05
特許番号
US04154852

関連ノート

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