Diethyl Oxalate → HCID 136007385, compound

HRID 1393895Notes

Reaction equation

HRID 1393895 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].N12CCCN=C1CCCCC2>>[CH2:16]([O:15][C:13](=[O:14])/[C:12](/[OH:18])=[CH:8]/[C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)[CH3:17]

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 136007385HCID 136007385, compoundYield 133.2%

Procedure

A mixture of 1.5 g (8.7 mmol) 2-chloro-4-methyl-5-nitropyridine (commercially available) in 5.88 mL (43.5 mmol) diethyl oxalate was treated with 2.34 ml (15.6 mmol) 1,8-diazabicylo[5.4.0]undec-7-ene and stirred for 4 h at room temperature. After evaporation of all volatiles the residue was acidified with 1N KHSO4 aq. and extracted with DCM. The combined organic layers were dried with MgSO4 and concentrated under reduced pressure to afford 3.16 g of the title compounds which was used without further purification in the next step.

Workup

  1. customAfter evaporation of all volatiles the residue
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6d3546d70df421eaa5e2245fbb8cf0c
Source dataset
uspto-grants-2008_03
Patent number
US07348323B2

Reaction notes

Loading…