(4-Aminophenoxy)benzene → 6-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrile

HRID 276863ノート

反応式

HRID 276863 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[O:15]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][N:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:26][C:25]1[CH:24]=[CH:23][C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 8764(4-Aminophenoxy)benzeneHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

生成物 1

HCID 185489566-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrile収率 69%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To 2.0 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 50 mL of methanol was added 2.2 g of 4-phenoxyaniline. After stirring the reaction under an inert atmosphere for 18 hr, the reaction mixture was poured into a mixture of brine and saturated aqueous sodium bicarbonate and the resultant crystals filtered and washed with water. The product was then recrystallized from chloroformhexanes. Drying in vacuo yielded 2.35 g (69%) of 6-fluoro-4-(4-phenoxy-phenylamino)-[1.7]naphthyridine-3-carbonitrile as yellow needles: melting point 211-213° C.; mass spectrum (m/e): M+H 356.9.

後処理

  1. customthe reaction under an inert atmosphere for 18 hr
  2. filtrationthe resultant crystals filtered
  3. washwashed with water
  4. customThe product was then recrystallized from chloroformhexanes
  5. customDrying in vacuo

出典と根拠

ORDレコード
ord-d0aa85005d3e41988f68ffd694a1f31c
出典データセット
uspto-grants-2002_03
特許番号
US06355636B1

反応ノート

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