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

HRID 2248587Notes

Reaction equation

HRID 2248587 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](CCCC)CCCC)=[O:12].C(N(C(C)C)CC)(C)C.C(COC)[O:32]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:32]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 222374N,N-Dibutyl-2-chloroacetamide

Product 1

HCID 578921Pyridine-2,3-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine diamide 6 was prepared according to the general procedure described in Example 8 using 2-(aminomethyl)pryidine (0.010 mol), 2-chloro-N,N-dibutylacetamide (0.030 mol), diisopropylethylamine (0.030 mol) and dimethoxyethane (30 mL). The product was isolated from the methylene chloride 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 (150°-200° C., 0.10 mm) to afford 3.6 g of product.

Workup

  1. extractionThe product was made basic by extraction with aqueous NaOH
  2. concentrationThe organic solution was concentrated
  3. distillationthe residue was distilled (150°-200° C., 0.10 mm)

Sources & evidence

ORD record
ord-6f4c734d90e6466f8f401384d1eed8f7
Source dataset
uspto-grants-1991_08
Patent number
US05041452

Reaction notes

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