Sodium Bicarbonate → 4-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile

HRID 612262

반응식

HRID 612262 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[Br:25])[NH2:21].C([O-])(O)=O.[Na+]>CCO>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[Br:25]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 5219813,4-DibromoanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

생성물 1

HCID 101146524-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile수율 31.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 6.20 g (26.6 mmol) of 4-chloro-6-nitroquinoline-3-carbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of EtOH was refluxed under N2 for 5 hr. Satd NaHCO3 was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and H2O and dried. The insoluble material was repeatedly extracted with boiling EtOAc and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of 4-(3,4-dibromophenylamino)-6-nitroquinoline-3-carbonitrile as a green solid: mass spectrum (electrospray, m/e): M+H 448.9.

후처리

  1. temperaturewas refluxed under N2 for 5 hr
  2. customvolatile material was removed
  3. customcollected
  4. washwashed with hexane and H2O
  5. customdried
  6. extractionThe insoluble material was repeatedly extracted with boiling EtOAc
  7. filtrationthe solution was then filtered through silica gel
  8. customThe solvent was removed

출처 및 근거

ORD 기록
ord-bbc4c360a2594a26ad6379e1c4b0f366
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

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