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

HRID 330362Notes

Reaction equation

HRID 330362 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-c9141a8133c64220abe46a7366cd7001
Source dataset
uspto-grants-1990_01
Patent number
US04895951

Reaction notes

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