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

HRID 2248584Notes

Reaction equation

HRID 2248584 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](CCCCCC)CCCCCC)=[O:12].C(N(C(C)C)CC)(C)C.C(COC)[O:36]C>CCCCCCC>[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:36]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 533169Chloroacetamide, N,N-dihexyl-

Product 1

HCID 578921Pyridine-2,3-dicarboxamide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Pyridine diamide 3 was prepared according to the general procedure described in Example 8 using 2-(aminomethyl)pyridine (0.015 mol), 2-chloro-N,N-dihexylacetamide (0.048 mol), diisopropylethylamine (0.033 mol) and dimethoxyethane (25 mL). The product was isolated from a heptane extraction of the acidic aqueous layer. The product was made basic by extraction with aqueous NaOH. The organic solution was concentrated, and the residue was distilled (200° C., 0.05 mm) to afford 6.1 g of pure product.

Workup

  1. extractionThe product was made basic by extraction with aqueous NaOH
  2. concentrationThe organic solution was concentrated
  3. distillationthe residue was distilled (200° C., 0.05 mm)

Sources & evidence

ORD record
ord-19a6b952101c40ec99b290a3bccd7ced
Source dataset
uspto-grants-1991_08
Patent number
US05041452

Reaction notes

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