4-Bromo-6,7-dimethyl-2,3-dihydro-1H-inden-1-one → 4-Cyano-6,7-dimethyl-1-indanone

HRID 2210937

反応式

HRID 2210937 の反応式
Br[C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13].[Cu][C:15]#[N:16]>CN(C=O)C.O.Cl.C1(C)C=CC=CC=1>[C:15]([C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:13])#[N:16]

参加物

7

反応物 2

HCID 138098694-Bromo-6,7-dimethyl-2,3-dihydro-1H-inden-1-oneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 190422934-Cyano-6,7-dimethyl-1-indanone

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 17.8 g (74.5 mmol) of 4-bromo-6,7-dimethyl-1-indanone [J. Het. Chem. 24, 677 (1987)] and 7.3 g (82 mmol) of copper(I) cyanide in 18 ml of DMF is stirred for 6 hours at 170°. The reaction mixture is then cooled to 100° and 200 ml of toluene and a solution of 31.2 g of iron(HI) chloride hexahydrate in 47 ml of water and 8.2 ml of concentrated hydrochloric acid are added in succession thereto. The reaction mixture is stirred for 20 minutes at 70°, cooled and diluted with toluene and water. The organic phase is separated off, washed with water, a semi-saturated sodium hydrogen carbonate solution and again with water, dried and concentrated by evaporation. The residue is crystallised from ethyl acetate and ether and corresponds to starting compound (a). Beige crystals having a melting point of 160°-163° are obtained; IR (CH2C12): 2220, 1710 cm-1.

後処理

  1. temperatureThe reaction mixture is then cooled to 100°
  2. stirringThe reaction mixture is stirred for 20 minutes at 70°
  3. temperaturecooled
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materiala semi-saturated sodium hydrogen carbonate solution and again with water, dried
  7. concentrationconcentrated by evaporation
  8. customThe residue is crystallised from ethyl acetate and ether and corresponds
  9. customare obtained

出典と根拠

ORDレコード
ord-30df6164520e4bc1b8555681c179edef
出典データセット
uspto-grants-1995_10
特許番号
US05461076

関連ノート

読み込み中…