Methanol → 3-nitro-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene-7-carbonitrile

HRID 1764721

반응식

HRID 1764721 반응식
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH:10]=[CH:11][C:12](=[O:13])[C:6]=2[CH:5]=1)([O-:3])=[O:2].CO.C(=O)([O-])[O-].[K+].[K+].CC(C)(O)[C:26]#[N:27]>O1CCCC1>[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][CH2:9][CH:10]([C:26]#[N:27])[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 887MethanolHCID 6406Acetone CyanohydrinHCID 11430Potassium CarbonateHCID 200947328,9-dihydro-3-nitro-5H-benzocyclohepten-5-one

생성물 1

HCID 545232963-nitro-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene-7-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

A mixture of 50 g of 3-nitro-8,9-dihydro [5H] benzocycloheptene-5-one, 1200 ml of methanol, 120 ml of tetrahydrofuran, 100 ml of a 10% aqueous potassium carbonate and 50 ml of acetone cyanhydrin under nitrogen was refluxed for an hour in a bath at 90° C. and the mixture was concentrated to about 200 ml under reduced pressure. The mixture was cooled to 20° C. and was extracted with methylene chloride. The organic phase was washed with water, dried and distilled to dryness under reduced pressure. The 58 g of brown oil residue were crystallized from 50 ml of methanol and the mixture was vacuum filtered to obtain 46 g of 3-nitro-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene-7-carbonitrile with a melting point of 107° C. and then 120° C.

후처리

  1. concentrationthe mixture was concentrated to about 200 ml under reduced pressure
  2. temperatureThe mixture was cooled to 20° C.
  3. extractionwas extracted with methylene chloride
  4. washThe organic phase was washed with water
  5. customdried
  6. distillationdistilled to dryness under reduced pressure
  7. customThe 58 g of brown oil residue were crystallized from 50 ml of methanol
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-2b0346b56d1d41af8c8e1dd4e1b2dc2c
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04117164

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