Hydrochloric Acid → 7-[(2-Chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1640200

반응식

HRID 1640200 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([OH:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Cl:15][C:16]1[CH:21]=[C:20]([O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH:8]([C:12]([OH:14])=[O:13])[CH2:9]3)=[CH:4][CH:3]=2)[CH:19]=[CH:18][N:17]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 7351522-Chloro-4-nitropyridineHCID 145412687-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

생성물 1

HCID 580552117-[(2-Chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid수율 52.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (5.62 g, 29.2 mmol); 2-chloro-4-nitropyridine (5.10 g, 32.2 mmol) and cesium carbonate (28.6 g, 87.7 mmol) in DMF (150 mL) was heated at 50° C. for 5 hr. The reaction mixture was allowed to cool to rt and acidified to pH 3 by addition of 1N HCl. The mixture was extracted with EtOAc and the organic solutions were combined, washed with water, dried over Na2SO4 and evaporated. The residue was adsorbed onto silica and purified by filtration through a pad of silica. The product was then triturated with EtOAc to give 7-[(2-chloropyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (4.62 g, 52.0%). LCMS: (FA) ES+ 304.1, ES− 302.1.

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. filtrationpurified by filtration through a pad of silica
  6. customThe product was then triturated with EtOAc

출처 및 근거

ORD 기록
ord-bf3a1acc90354465b1e8cdbb4a1fe2ab
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

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