홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Cesium carbonate → 3-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 852666
노트
인쇄 미리보기

반응식

HRID 852666 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:14]([O-:17])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O1CCOCC1>[N+:11]([C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([N:11]2[CH2:9][CH2:8][CH2:4][C:14]2=[O:17])[CH:10]=1)[C:5]([OH:7])=[O:6])([O-:13])=[O:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 10796Cesium carbonateHCID 2393363-Bromo-5-nitrobenzoic acid

생성물 1

HCID 222530233-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acid수율 148.7%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium
촉매
HCID 312751,4-Dioxane용매

실험 절차

A flask was charged under nitrogen with 3-bromo-5-nitro-benzoic acid (D5) (12.3 g, 50 mmol, 1 equiv), Cs2CO3 (24.4 g, 75 mmol, 1.5 equiv), tris(dibenzylideneacetone)dipalladium(0) (229 mg, 0.25 mmol, 0.005 equiv), Xantphos (433 mg, 0.75 mmol, 0.015 equiv) and dioxan (120 ml). 2-Pyrrolidin-2-one (5.7 ml, 75 mmol, 1.5 equiv) was then added via syringe and the resulting mixture was stirred at reflux for 60 h then cooled to room temperature and concentrated in vacuo. The residue was diluted with H2O and 1N aqueous NaOH solution and extracted twice with Et2O. The aqueous phase was then acidified to pH 1 and extracted three times with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give 3-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A27) (9.3 g, 75%) as a pale brown solid.

후처리

  1. temperatureat reflux for 60 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with H2O and 1N aqueous NaOH solution
  4. extractionextracted twice with Et2O
  5. extractionextracted three times with AcOEt
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6cebce2ac16e40bd8e118f207827b04f
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253198B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트