Ammonia → 4-Chloroisoquinoline

HRID 10548

反応式

HRID 10548 の反応式
N[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.N([O-])=O.[Na+].N.[ClH:17]>[Cu]Cl>[Cl:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1

参加物

6

反応物 4

HCID 222AmmoniaHCID 313Hydrochloric Acid2 回HCID 902374-AminoisoquinolineHCID 23668193Sodium Nitrite

生成物 1

HCID 6409744-Chloroisoquinoline

試薬・触媒・溶媒 1

HCID 62652Cuprous chloride触媒

実験手順

Intermediate 87 (1.27 g) was dissolved in 1 N aqueous hydrochloric acid (36 ml) and added dropwise with an aqueous solution (36 ml) of sodium nitrite (1.21 g, Wako Pure Chemical Industries) with ice cooling. The obtained suspension was added dropwise to a solution of copper(I) chloride (1.83 g, Wako Pure Chemical Industries) in 1 N aqueous hydrochloric acid (20 ml) with ice cooling, then warmed to room temperature and stirred for 15 hours. The reaction mixture was added with 28% aqueous ammonia (50 ml) and extracted twice with ethyl acetate (150 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (433 mg).

後処理

  1. extractionextracted twice with ethyl acetate (150 ml for each time)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-6e55001f2da4432ebe9991fc4a77c3aa
出典データセット
uspto-grants-2006_08
特許番号
US07094789B2

関連ノート

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