Pyridine → N-[1,1'-biphenyl]-4-yl-3-hydroxy-4-methoxybenzamide

HRID 1057990노트

반응식

HRID 1057990 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.BrN1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:43][CH:42]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O>[C:44]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:43]=[CH:42][C:41]([NH:40][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([OH:1])[CH:3]=2)=[CH:46][CH:45]=1

참가 물질

8

반응물 5

HCID 1049PyridineHCID 71024-AminobiphenylHCID 11776TriphenylphosphineHCID 12575Isovanillic AcidHCID 67184N-bromobutanimide

생성물 1

HCID 18672541N-[1,1'-biphenyl]-4-yl-3-hydroxy-4-methoxybenzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-20 °C

실험 절차

A solution of 3-hydroxy-4-methoxybenzoic acid (0.5 g, 3 mmol) in dichloromethane and dimethylformamide was cooled to −20° C., and N-bromosuccinimide (0.57 g, 3.2 mmol) and triphenylphosphine (0.8 g, 3.1 mmol) were added in one portion. The mixture was stirred at −20° C. for 10 min, and treated with a solution of 4-aminobiphenyl (0.5 g, 3 mmol) and dry pyridine (0.3 g, 3.8 mmol) in dichloromethane (5 mL). The mixture was allowed to warm to RT, stirred 20 h, concentrated in vacuo, and the residue was stirred in 5% methanol/dichloromethane (40 mL) and filtered. The filtrate was concentrated in vacuo, chromatographed (silica gel, 5% methanol/dichloromethane), and fractions containing the product were pooled, concentrated in vacuo, and dissolved in dichloromethane from which the title compound precipitated (0.11 g): MS(ES) m/e 320 [M+H]+.

후처리

  1. temperatureto warm to RT
  2. stirringstirred 20 h
  3. concentrationconcentrated in vacuo
  4. stirringthe residue was stirred in 5% methanol/dichloromethane (40 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customchromatographed (silica gel, 5% methanol/dichloromethane), and fractions
  8. additioncontaining the product
  9. concentrationconcentrated in vacuo
  10. dissolutiondissolved in dichloromethane from which the title compound
  11. customprecipitated (0.11 g)

출처 및 근거

ORD 기록
ord-4962bf54bedf4e9a921681acab13d46a
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515027B1

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