Ammonium Chloride → 6-Amino-4-[(3-bromo-4-fluorophenyl)amino]-7-methoxy-3-quinolinecarbonitrile

HRID 612134노트

반응식

HRID 612134 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH3:24])=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:25]#[N:26])[CH:5]=[CH:6][C:7]=1[F:8].[Cl-].[NH4+]>O.CO.C(OCC)(=O)C.[Fe]>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:23][CH3:24])[N:13]=[CH:12][C:11]([C:25]#[N:26])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=1

참가 물질

7

반응물 2

HCID 25517Ammonium ChlorideHCID 224666584-[(3-Bromo-4-fluorophenyl)amino]7-methoxy-6-nitro-quinoline-3-carbonitrile

생성물 1

HCID 224666136-Amino-4-[(3-bromo-4-fluorophenyl)amino]-7-methoxy-3-quinolinecarbonitrile수율 78.4%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2.9 g (6.95 mmol) of 4-[(3-bromo-4-fluorophenyl)amino]7-methoxy-6-nitro-quinoline-3-carbonitrile, 6.5 g (121.6 mmol) of ammonium chloride and 4.05 g (73 mmol) of iron in 50 ml of water and 50 ml of methanol for 6 hours. The mixture was diluted with hot ethyl acetate and the hot mixture was filtered. The filtration was washed with saturated sodium chloride solution then the organic layer was dried over sodium sulfate. The solvent was removed and the residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol to give 2.11 g of light yellow solid: mass spectrum (electrospray, m/e): M+H 386.7 and 388.8.

후처리

  1. filtrationthe hot mixture was filtered
  2. filtrationThe filtration
  3. washwas washed with saturated sodium chloride solution
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol

출처 및 근거

ORD 기록
ord-66c58c14b1c44930ac7840701fce9e5c
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002008

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