Ethanol → Ethyl 6-bromonicotinate

HRID 842695Notes

Reaction equation

HRID 842695 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 14784668Ethyl 6-bromonicotinateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2d91dec768aa4e6bb696860f466d54d7
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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