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

HRID 1935186

反応式

HRID 1935186 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1e8a7058d5246a3bd22db9d1866d7c9
出典データセット
uspto-grants-2002_05
特許番号
US06384051B1

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