Methanol → 6-Amino-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinoline-3-carbonitrile

HRID 396180ノート

反応式

HRID 396180 の反応式
[Cl: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+].CO>[Fe].O>[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]([Cl:1])[CH:3]=1

参加物

6

反応物 3

HCID 887MethanolHCID 25517Ammonium Chloride2 回HCID 108940424-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile

生成物 1

HCID 111424366-Amino-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinoline-3-carbonitrile収率 8,428.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒2 回HCID 962Water溶媒

実験手順

An amount of 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile (9.9 g, 0.27 mmol) was combined with ammonium chloride (11.4 g, 0.21 mol), iron powder (8.9 g, 0.16 mol), methanol (200 mL), and water (50 mL), and heated at reflux for 2 hours. An additional amount of iron (1.0 g, 0.018 mol) and ammonium chloride (1.0 g, 0.019 mol) were added and the mixture was refluxed for an additional 3.5 hours. The reaction mixture was filtered hot and the residue was washed with boiling methanol to extract the product. The filtrate was evaporated to a slurry and stirred with saturated sodium bicarbonate solution and ethyl acetate. The layers were separated, and the organic layer was dried over magnesium sulfate and evaporated to dryness to give a green powder (7.8 g, 85%), which was used without further purification.

後処理

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperaturethe mixture was refluxed for an additional 3.5 hours
  4. filtrationThe reaction mixture was filtered hot
  5. washthe residue was washed with boiling methanol
  6. extractionto extract the product
  7. customThe filtrate was evaporated to a slurry
  8. customThe layers were separated
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. customevaporated to dryness

出典と根拠

ORDレコード
ord-3a1ebcfdbce44adea798666851fc9715
出典データセット
uspto-grants-2003_08
特許番号
US06608048B2

反応ノート

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