2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Isopropyl-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

HRID 573784

반응식

HRID 573784 반응식
[C:1]([C:6]1[C:7](=[O:16])[O:8][C:9]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:10]=1)(=O)[CH:2]([CH3:4])[CH3:3].[NH2:17][C:18]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20](=[O:26])[CH:19]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>ClCCl.CCOCC.C(OC(=O)C)C>[CH:2]([C:1]1[C:6]2[C:7](=[O:16])[O:8][C:9]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:10]=2[C:19]2[C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH2:23][C:18]=2[N:17]=1)([CH3:4])[CH3:3]

참가 물질

8

반응물 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 54670067L-Ascorbic AcidHCID 66762855HCID 66762855, 화합물

생성물 1

HCID 667623744-Isopropyl-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
200 °C

실험 절차

3.12 g 3-Isobutyryl-1,8-dioxaspiro[4.5]dec-3-en-2-one and 2.13 g 3-amino-5,5-dimethylcyclohex-2-enone are mixed and heated to 200° C. for 10 minutes under a vacuo of 20 mbar. The mixture is cooled to room temperature, 15 ml ethylacetate are added and the mixture is stirred for 30 minutes. Then 15 ml petrole ether are added and the precipitate is isolated by filtration. The crude product is dissolved in 350 ml dichloromethane, treated with 2.46 g 2,3dichloro-5,6-dicyano-p-benzoquinone and stirred for 18 hours. 2 g Ascorbic acid are added and the mixture is stirred for 10 minutes. The it is washed for three times with water. The organic phase is dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50).

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. customthe precipitate is isolated by filtration
  3. stirringstirred for 18 hours
  4. stirringthe mixture is stirred for 10 minutes
  5. washThe it is washed for three times with water
  6. dry with materialThe organic phase is dried with sodium sulphate
  7. customthe solvents are evaporated in vacuo
  8. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50)

출처 및 근거

ORD 기록
ord-c8c75e02cd2941df9fceb65ab2620aad
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029544B2

연결된 노트

불러오는 중…