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

HRID 501636노트

반응식

HRID 501636 반응식
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]

참가 물질

10

반응물 4

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

생성물 1

HCID 534162084-Amino-2-chloro-3-fluorobenzonitrile수율 99.2%

시약·촉매·용매 5

HCID 24463Copper sulfate pentahydrate촉매HCID 284Formic Acid용매HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ad3250a4e1084c13be80de2281f24ca5
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772267B2

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