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

HRID 2248588Notes

Reaction equation

HRID 2248588 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](C(C)C)C(C)C)=[O:12].C(N(C(C)C)CC)(C)C.C(COC)[O:30]C>>[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:30]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 1390132-chloro-N,N-bis(propan-2-yl)acetamide

Product 1

HCID 578921Pyridine-2,3-dicarboxamide

Procedure

Pyridine diamide 7 was prepared according to the general procedure described in Example 8 using 2-(aminomethyl)pyridine (0.013 mol), 2-chloro-N,N-diisopropylacetamide (0.038 mol), diisopropylethylamine (0.038 mol) and dimethoxyethane (25 mL). The product was isolated from both the methylene chloride extraction of the acidic aqueous layer and the heptane extraction of the basic layer in about equal amounts. Mass spectral analysis of the two layers showed the material in the heptane layer to be of greater purity. The residue from the heptane layer was distilled (150° C., 0.05 mm) to afford 2.2 g of product.

Workup

  1. customThe product was isolated from both
  2. extractionthe methylene chloride extraction of the acidic aqueous layer
  3. extractionthe heptane extraction of the basic layer in about equal amounts
  4. distillationThe residue from the heptane layer was distilled (150° C., 0.05 mm)

Sources & evidence

ORD record
ord-50b4d1fb0aa4433cbc09ac788bb4f5aa
Source dataset
uspto-grants-1991_08
Patent number
US05041452

Reaction notes

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