Pyridine → HCID 58083713, compound

HRID 558029

Reaction equation

HRID 558029 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:7]=1)[CH3:5].N1C=CC=CC=1.[Br:24][CH2:25][C:26](Cl)=[O:27]>ClCCl>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:26](=[O:27])[CH2:25][Br:24])[CH:12]=2)[CH:7]=1)[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 89602Bromoacetyl chlorideHCID 5988972-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester

Product 1

HCID 58083713HCID 58083713, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester (20 grams) and pyridine (10.3 grams) in dichloromethane (200 ml) maintained at 0-5° C. under N2 atmosphere was added dropwise bromoacetyl chloride (19.6 grams). The reaction was stirred at the same temperature for one hour. The reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate followed by drying over sodium sulphate and distillation to get crude compound, which was purified by column chromatography using hexane as eluant to get pure 2-[6-(2-bromo-acetoxy)-naphthalen-2-yl]-propionic acid methyl ester (14 grams) as a dark brown syrup. The pure product was characterized using 1H NMR spectroscopy in CDCl3 δ 1.55 (d, 3H, CH3), 3.65 (s, 3H, Ester), 3.82 (q, 1H, CH), 4.08 (s, 2H, OCH2) 7.20 (dd, 1H, Ar), 7.4 (dd, 1H, Ar), 7.57 (d, 1H, Ar), 7.72 (d, 1H, Ar), 7.78 (d, 1H, Ar), 7.84 (d, 1H, Ar).

Workup

  1. washThe reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate
  2. dry with materialby drying over sodium sulphate and distillation
  3. customto get crude compound, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3fefca0c207647a582ef51a034ddd878
Source dataset
uspto-grants-2011_11
Patent number
US08062653B2

Linked notes

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