1,2-Dimethoxyethane → Pyridine-2,3-dicarboxamide

HRID 330359Notes

Reaction equation

HRID 330359 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.ClC[C:11]([N:13](CC)CC)=[O:12].C(N(C(C)C)CC)(C)C.C(COC)[O:28]C>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:11]([NH2:13])=[O:12])[C:3]=1[C:2]([NH2:1])=[O:28]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 16844Chloro-N,N-diethylacetamideHCID 195092-PyridinemethanamineHCID 81531Diisopropylethylamine

Product 1

HCID 578921Pyridine-2,3-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine diamide 2 was prepared according to the general procedure described in Example 8 using 2-(aminomethyl)pyridine (0.015 mol), 2-chloro-N,N-diethylacetamide (0.045 mol), diisopropylethylamine (0.060 mol) and dimethoxyethane (25 mL). The product was isolated from the methylene chloride extraction of the basic aqueous layer. The residue was distilled (140° C., 0.10 mm) to afford 3.7 g of pure product.

Workup

  1. distillationThe residue was distilled (140° C., 0.10 mm)

Sources & evidence

ORD record
ord-2feade2e254b4888b75c86a856b753be
Source dataset
uspto-grants-1990_01
Patent number
US04895951

Reaction notes

Loading…