Ethyl diazoacetate → HCID 22498670, compound

HRID 1814763Notes

Reaction equation

HRID 1814763 reaction equation
C([O:3][C:4](=[O:17])[C:5](=[N+:15]=[N-:16])[C:6]([C:8]1[C:9](Cl)=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:7])C.ClC1N=CC=CC=1C(Cl)=O.[N+](=CC(OCC)=O)=[N-]>>[O:7]=[C:6]1[C:5]([C:4]([OH:3])=[O:17])=[N:15][NH:16][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]1=2

Participants

3

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86759633HCID 86759633, compound

Product 1

HCID 22498670HCID 22498670, compoundYield 204.1%

Procedure

3-(2-Chloropyridin-3-yl)-2-diazo-3-oxopropionic acid ethyl ester—2-Chloronicotinoyl chloride (10 g) and ethyl diazoacetate (19.4 g) were heated together at 55° C. for 3 hours then left at ambient temperature for 18 hours. The mixture was concentrated in vacuo and the residue chromatographed on silica gel, eluting with 30-50% ethyl acetate in hexane. This gave the title compound (9.08 g, 63%). NMR (CDCl3) δ1.15 (3H, t), 4.15 (2H, q), 7.25 (1H, t), 7.58 (1H, dd), 8.48 (1H, dd).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue chromatographed on silica gel
  3. washeluting with 30-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-624f4c810b6549b7b78f675a2f8654f0
Source dataset
uspto-grants-2005_04
Patent number
US06878704B2

Reaction notes

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