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

HRID 330363Notes

Reaction equation

HRID 330363 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)pyridine (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-2d5411438995407a8aed364ea93d54cb
Source dataset
uspto-grants-1990_01
Patent number
US04895951

Reaction notes

Loading…