Water → 3-Aminomethyl-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinolin-2-ylamine

HRID 392183노트

반응식

HRID 392183 반응식
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:9]2[CH2:8][CH2:7][C:6]3[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=3[C:4]=2[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(OCC)(=O)C>C1COCC1>[NH2:13][CH2:12][C:11]1[C:2]([NH2:1])=[N:3][C:4]2[C:5]3[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=3[CH2:7][CH2:8][C:9]=2[C:10]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 226635122-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile

생성물 1

HCID 102157313-Aminomethyl-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinolin-2-ylamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under an atmosphere of argon, a solution of 2-amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile (200 mg, 0.58 mmol) in THF (1 ml) is added slowly to a suspension of LiAlH4 (162 mg, 4.26 mmol) in THF (1 ml). After stirring for 2 h at room temperature, the reaction mixture is cooled to −20° C. and water (0.2 ml) is added. After 15 min, ethyl acetate is added and the mixture is filtered through Decalite. The organic phase is then separated, washed with water, and dried over sodium sulfate. Purification by flash chromatography (silica gel, methanol, dichloromethane) affords the title compound, MS: m/e=369.9 (M+H+), as a light yellow solid (53 mg, 26%).

후처리

  1. temperaturethe reaction mixture is cooled to −20° C.
  2. waitAfter 15 min
  3. filtrationthe mixture is filtered through Decalite
  4. customThe organic phase is then separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customPurification by flash chromatography (silica gel, methanol, dichloromethane)

출처 및 근거

ORD 기록
ord-e58ca9f83b63477d95cbf5d99ecb7fd1
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800650B2

반응 노트

불러오는 중…