Pyridine → 7-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

HRID 914925노트

반응식

HRID 914925 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.N1C=CC=CC=1.[I-].[K+]>C(O)C>[I:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:3][C:4]([CH3:13])=[N:5]2)=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 4875Potassium IodideHCID 31268PyrrolidineHCID 220545164-Chloro-7-iodo-2-methylquinoline

생성물 1

HCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline수율 87%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A suspension of 2 g of 4-chloro-7-iodo-2-methyl-quinoline (European patent application EP 0497371, CA 143946-47-8) in 20 ml absolute ethanol is treated successively with 1.09 ml pyrrolidine, 0.2 ml pyridine and 50 mg potassium iodide under argon. The resulting mixture is refluxed for 24 h. The solvent is then distilled off. The residue is taken up in 50 ml water and basified to pH 12 with a 2N solution of sodium hydroxyde. The solid is filtered upon precipitation and washed with 20 ml of water and 20 ml of diethylether. The final product is dried under vacuum yielding 1.95 g (87%) of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline as an off-white solid. Mp: 99-102° C. MS (EI): peaks at m/e: 338(M+, 100%), 296 (5%), 183(9%).

후처리

  1. temperatureThe resulting mixture is refluxed for 24 h
  2. distillationThe solvent is then distilled off
  3. filtrationThe solid is filtered upon precipitation
  4. washwashed with 20 ml of water and 20 ml of diethylether
  5. dry with materialThe final product is dried under vacuum

출처 및 근거

ORD 기록
ord-0b28f60bb2514b28af623454d5e1c84f
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265125B2

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