Phosphorus oxychloride → 4-Chloro-2-methyl-10-(2,4,6-trimethylphenyl)pyrido[2,3-b]indolizine

HRID 2299263노트

반응식

HRID 2299263 반응식
O[C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178424432HCID 178424432, 화합물

생성물 1

HCID 155132734-Chloro-2-methyl-10-(2,4,6-trimethylphenyl)pyrido[2,3-b]indolizine수율 94%

실험 절차

A solution of 4-hydroxy-2-methyl-10-(2,4,6-trimethylphenyl)pyrido-[2,3-b]indolizine (10.1 g; 32 mmol) in phosphorus oxychloride (60 mL) is heated at 100° C. for 1 hour, cooled to room temperature, and concentrated in vacuo. The residue is partitioned into ice water and dichloromethane. The aqueous phase is separated and extracted twice with dichloromethane. The combined organics are washed with a 1 N aqueous sodium hydroxide solution and then with water. The solution is dried (Na2SO4), filtered, and concentrated in vacuo, and the resulting dark residue is filtered through a short pad of silica gel and washed with 25% ethyl acetate in hexane. The filtrate is concentrated in vacuo to give 10.1 g of the title compound as a yellow solid (94%): 1H nmr (400 MHz, CDCl3) d 2.00 (s, 6 H), 2.37 (s, 3 H), 2.64 (s, 3 H), 6.58 (t, 1 H), 6.95 (dd, 1 H), 7.00 (s, 2 H), 7.07 (s, 1 H), 7.08 (d, 1 H), 9.26 (d, 1 H).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue is partitioned into ice water and dichloromethane
  3. customThe aqueous phase is separated
  4. extractionextracted twice with dichloromethane
  5. washThe combined organics are washed with a 1 N aqueous sodium hydroxide solution
  6. dry with materialThe solution is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationthe resulting dark residue is filtered through a short pad of silica gel
  10. washwashed with 25% ethyl acetate in hexane
  11. concentrationThe filtrate is concentrated in vacuo

출처 및 근거

ORD 기록
ord-dd8b81382aaa4d1ebf00d71a4988b8ba
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495686B2

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