Triethylamine → 4-Amino-2-chloro-3-fluorobenzonitrile

HRID 501636ノート

反応式

HRID 501636 の反応式
Cl.NO.[NH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[C:7]([Cl:13])[C:6]=1[F:14].C([N:17](CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1>O.C(Cl)Cl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].C(O)=O.N1C=CC=CC=1>[NH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:17])=[C:7]([Cl:13])[C:6]=1[F:14]

参加物

10

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 443297Hydroxyamine hydrochlorideHCID 597543024-Amino-2-chloro-3-fluorobenzaldehyde

生成物 1

HCID 534162084-Amino-2-chloro-3-fluorobenzonitrile収率 99.2%

試薬・触媒・溶媒 5

HCID 24463Copper sulfate pentahydrate触媒HCID 284Formic Acid溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of hydroxylamine hydrochloride (336 mg, 4.84 mmol) in water (1.2 mL) was added 4-amino-2-chloro-3-fluorobenzaldehyde (73A) (0.800 g, 4.61 mmol) and pyridine (2.5 mL). After stirring at rt for 1 h, copper (II) sulfate pentahydrate (230 mg, 0.922 mmol) was added followed by a solution of triethylamine (1.40 mL, 9.68 mmol) in CH2Cl2 (2.5 mL). To the resulting dark green reaction mixture was then added a solution of DCC (1.14 g, 5.53 mmol) in CH2Cl2 (10 mL) and the reaction was stirred for 2 h. Formic acid (1 mL) was added and the reaction was stirred for 20 min, filtered through celite, and concentrated. The resulting residue was purified via silica gel chromatography eluting with 20-30% EtOAc/hexane to provide the title compound (0.780 g) as a light brown solid.

後処理

  1. stirringthe reaction was stirred for 2 h
  2. stirringthe reaction was stirred for 20 min
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customThe resulting residue was purified via silica gel chromatography
  6. washeluting with 20-30% EtOAc/hexane

出典と根拠

ORDレコード
ord-ad3250a4e1084c13be80de2281f24ca5
出典データセット
uspto-grants-2010_08
特許番号
US07772267B2

反応ノート

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