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

HRID 330361Notes

Reaction equation

HRID 330361 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.ClC[C:11]([NH:13]C(C)(C)CC(C)(C)C)=[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 3524332-chloro-N-(1,1,3,3-tetramethylbutyl)acetamide

Product 1

HCID 578921Pyridine-2,3-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine diamide 4 was prepared according to the general procedure described in Example 8 using 2-(aminomethyl)pyridine (0.011 mol), 2-chloro-N-(1,1,3,3,-tetramethylbutyl)acetamide (0.033 mol), diisopropylethylamine (0.025 mol) and dimethoxyethane (25 mL). The product was isolated from the methylene chloride extraction of the acidic aqueous layer. The product was made basic by extraction of the methylene chloride solution with aqueous NaOH. The methylene chloride solution was concentrated, and the residue was distilled (150° C., 0.03 mm) to afford 3.7 g of pure product.

Workup

  1. extractionThe product was made basic by extraction of the methylene chloride solution with aqueous NaOH
  2. concentrationThe methylene chloride solution was concentrated
  3. distillationthe residue was distilled (150° C., 0.03 mm)

Sources & evidence

ORD record
ord-31842623b17d4ff58481920f0a65a183
Source dataset
uspto-grants-1990_01
Patent number
US04895951

Reaction notes

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