1,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2) → 4-(3-Dimethylamino-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile

HRID 612157

반응식

HRID 612157 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].Cl.Cl.[CH3:20][N:21]([CH3:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1.C(OC(O)C)C>N1C=CC=CC=1>[CH3:20][N:21]([CH3:29])[C:22]1[CH:23]=[C:24]([NH:28][C:2]2[C:11]3[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=3[O:12][CH3:13])[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:25]=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 101298981-EthoxyethanolHCID 224665354-Chloro-5,8-dimethoxyquinoline-3-carbonitrile

생성물 1

HCID 224667364-(3-Dimethylamino-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile수율 77.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 0.148 g of 4-chloro-5,8-dimethoxy-3-quinolinecarbonitrile, 0.146 g of N,N-dimethyl-1,3-phenylenediamine dihydrochloride, 0.2 ml of pyridine, and 5 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. Then the mixture was partitioned between ethyl acetate and saturated sodium chloride solution. The organic layer was dried and concentrated in vacuo. The residue thus obtained was chromatographed on silica gel eluting with ethyl acetate. Solvent was removed from product fractions giving 0.160 g of 4-(3-dimethylamino-phenylamino)-5,8-dimethoxy-quinoline-3-carbonitrile as a solid, mp 103-105° C.; mass spectrum (EI, m/e): M 348.1588.

후처리

  1. temperatureat reflux temperature for 30 minutes
  2. customThen the mixture was partitioned between ethyl acetate and saturated sodium chloride solution
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue thus obtained
  6. customwas chromatographed on silica gel eluting with ethyl acetate
  7. customSolvent was removed from product fractions

출처 및 근거

ORD 기록
ord-9a9221bcd5094dbea5d4910619fe94c9
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

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