Pyridine → HCID 11694252, compound

HRID 1669344Notes

Reaction equation

HRID 1669344 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][O:9][C:10](=[O:13])[CH2:11][NH2:12].[CH:14]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20])=[O:15]>O1CCCC1>[CH3:8][O:9][C:10]([CH2:11][NH:12][C:14]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[CH:19]=[O:20])=[O:15])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 122755Glycine methyl ester hydrochlorideHCID 152388213-Formylbenzoyl chloride

Product 1

HCID 11694252HCID 11694252, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 200 ml of tetrahydrofuran, 26.00 g of pyridine and 20.70 g of glycine methyl ester hydrochloride was added a solution of 16.00 g of 3-formylbenzoic acid chloride in 20 ml of tetrahydrofuran at 10° C. After stirred at room temperature for 60 hours, insolubles were filtered and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 4.23 g of oily 3-[[(methyoxycarbonylmethyl)amino]carbonyl]benzaldehyde [Compound No. (b)].

Workup

  1. filtrationinsolubles were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b60eb7571d2540848d028fe1cfcadcef
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

Loading…