Ethanol → Ethyl 6-bromonicotinate

HRID 842695

반응식

HRID 842695 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.[CH2:11](OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)[CH3:12].C(O)C>ClCCl>[CH2:11]([O:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[N:3][CH:4]=1)=[O:10])[CH3:12]

참가 물질

5

반응물 3

HCID 702EthanolHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 2389326-Bromonicotinic acid

생성물 1

HCID 14784668Ethyl 6-bromonicotinate수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-bromopyridine-5-carboxylic acid (J.Org.Chem., 12, 456 (1947)) (2.32 g, 11.49 mmol) and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (3.12 g, 12.64 mmol) in dichloromethane (30 ml) was stired at room temperature for 1 hour under nitrogen. Absolute ethanol (5 ml) was added and the mixture stirred for 30 minutes and then concentrated under reduced pressure. The residue was partitioned between dichloromethane (40 ml) and 10% w/w aqueous potassium carbonate solution (40 ml). The aqueous layer was extracted with dichloromethane (25 ml) and the combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel, eluting with dichloromethane gave 2-bromopyridine-5-carboxylic acid ethyl ester (2.18 g, 83%) as a colourless oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane (40 ml) and 10% w/w aqueous potassium carbonate solution (40 ml)
  3. extractionThe aqueous layer was extracted with dichloromethane (25 ml)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel
  7. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-2d91dec768aa4e6bb696860f466d54d7
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376490B1

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