3-Amino-5,5-dimethyl-2-cyclohexen-1-one → 9-(4-fluoro-3-chlorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

HRID 1275811

반응식

HRID 1275811 반응식
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[Cl:20]>C(O)C.Cl>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[C:3]3[C:4](=[O:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]=3[NH:1][C:2]3[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]2=3)=[CH:14][C:13]=1[Cl:20]

참가 물질

5

반응물 2

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 5938663-Chloro-4-fluorobenzaldehyde

생성물 1

HCID 221178659-(4-fluoro-3-chlorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione수율 15%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

A solution of 1.39 g of 3-amino-5,5-dimethyl-2-cyclohexen-1-one and 793 mg of 4-fluoro-3-chlorobenzaldehyde in 10 ml of absolute ethanol and 1 ml of 1M aqueous hydrochloric acid was heated at reflux under a nitrogen atmosphere for 18 hours. The cooled mixture was filtered and the residue was washed with 25 ml of cold diethyl ether. Crystallization from absolute ethanol/water gave 302 mg of 9-(4-fluoro-3-chlorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione as a pale yellow crystalline solid of melting point 274-275° C. (decomposition).

후처리

  1. temperatureat reflux under a nitrogen atmosphere for 18 hours
  2. filtrationThe cooled mixture was filtered
  3. washthe residue was washed with 25 ml of cold diethyl ether
  4. customCrystallization from absolute ethanol/water

출처 및 근거

ORD 기록
ord-b99ac60c40c04bb0b444bf70fad63edf
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162918

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