Methanol → 6-Amino-4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethyloxyquinoline

HRID 1935186

반응식

HRID 1935186 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH3:26])=[C:18]([N+:21]([O-])=O)[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:27]#[N:28])[CH:6]=[CH:7][C:8]=1[F:9].[Cl-].[NH4+].CO>O.[Fe]>[NH2:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[O:24][CH2:25][CH3:26])[N:14]=[CH:13][C:12]([C:27]#[N:28])=[C:11]2[NH:10][C:5]1[CH:6]=[CH:7][C:8]([F:9])=[C:3]([Cl:2])[CH:4]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 224665794-((3-Chloro-4-fluorophenyl)amino)-7-ethoxy-6-nitroquinoline-3-carbonitrile hydrochloride

생성물 1

HCID 110356856-Amino-4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethyloxyquinoline

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

4-(3-Chloro-4-fluoro-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile hydrochloride (38.6 g 91.2 mmol) was mixed with 35.7 g (638 mmol) of iron powder. A solution of 43.9 g (820 mmol) of ammonium chloride in 280 ml of water was added followed by 985 ml of methanol. The mixture was reflux with mechanical stirring under nitrogen for 4 hr at which time TLC indicated complete reduction. The reaction mixture was filtered hot and solids were washed with 500 ml of boiling methanol. After the combined filtrate was evaporated, the residue was partitioned between 1.5L of warm ethyl acetate and 700 ml of saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, treated with Norite, filtered and evaporated to give a solid which was recrystallized from CHCl3-hexanes giving 29.0 g (89%) of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile as a light green solid.

후처리

  1. temperatureThe mixture was reflux
  2. filtrationThe reaction mixture was filtered hot
  3. washsolids were washed with 500 ml of boiling methanol
  4. customAfter the combined filtrate was evaporated
  5. customthe residue was partitioned between 1.5L of warm ethyl acetate and 700 ml of saturated sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. additiontreated with Norite
  8. filtrationfiltered
  9. customevaporated
  10. customto give a solid which
  11. customwas recrystallized from CHCl3-hexanes giving 29.0 g (89%) of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile as a light green solid

출처 및 근거

ORD 기록
ord-b1e8a7058d5246a3bd22db9d1866d7c9
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384051B1

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