Thionyl Chloride → 1-Chloro-4-chloromethyl-3-methyl-isoquinoline

HRID 606304

반응식

HRID 606304 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=O)=[C:10]([CH3:20])[N:9]=1.O=S(Cl)[Cl:23]>C1COCC1.C(Cl)Cl>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][Cl:23])=[C:10]([CH3:20])[N:9]=1

참가 물질

6

반응물 3

HCID 24386Thionyl ChlorideHCID 21226445Aluminium lithium hydrideHCID 86615929HCID 86615929, 화합물

생성물 1

HCID 866159311-Chloro-4-chloromethyl-3-methyl-isoquinoline수율 90%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

LAH (3.6 ml of 1M in THF, 3.62 mmol) is added to a solution of 1-chloro-3-methyl-isoquinoline-4-carbaldehyde (744 mg, 3.62 mmol) in THF (10 ml) at 0° C. After stirring for 30 min at ambient temperature, the mixture is quenched with small amounts of saturated sodium sulfate and filtered through a pad of celite. The filtrate is concentrated in vacuo to give the crude alcohol. SOCl2 (13 ml of 2M in DCM, 25 mmol) is added to a solution of the crude alcohol in DCM (5 ml). After stirring for 1 h at room temperature, the mixture is concentrated in vacuo and the residue is chromatographed on silica gel to give 737 mg of 1-chloro-4-chloromethyl-3-methyl-isoquinoline. 1H NMR (CDCl3) 8.44 (d, 1H), 8.18 (d, 1H), 8.02 (t, 1H), 7.82 (t, 1H), 5.03 (s, 2H), 3.00 (s, 3H).

후처리

  1. customthe mixture is quenched with small amounts of saturated sodium sulfate
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give the crude alcohol
  5. stirringAfter stirring for 1 h at room temperature
  6. concentrationthe mixture is concentrated in vacuo
  7. customthe residue is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-5c0e840b92554b8ba569216e3d66857b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915288B2

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