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

HRID 2248586Notes

Reaction equation

HRID 2248586 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](CCCCCCCC)CCCCCCCC)=[O:12].C(N(C(C)C)CC)(C)C.C(COC)[O:40]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:40]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 2224152-chloro-N,N-dioctylacetamide

Product 1

HCID 578921Pyridine-2,3-dicarboxamide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Pyridine diamide 5 was prepared according to the general procedure described in Example 8 using 2-(aminomethyl)pyridine (0.019 mol), 2-chloro-N,N-dioctylacetamide (0.056 mol), diisopropylethylamine (0.056 mol) and dimethoxyethane (30 mL). The product was isolated from the 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 (150°-200° C., 0.10 mm).

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-72092b96b7d543d288103238d8cb42c7
Source dataset
uspto-grants-1991_08
Patent number
US05041452

Reaction notes

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