Dimethylformamide → HCID 12795068, compound

HRID 647994Notes

Reaction equation

HRID 647994 reaction equation
I[CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[C:6]1[CH2:14][C:15]([O:17][CH3:18])=[O:16].[H-].[Na+].CN(C)C=O>[Na+].[Cl-]>[C:7]1([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:9][N:5]2[CH2:4][CH2:3][CH2:2][CH:14]([C:15]([O:17][CH3:18])=[O:16])[C:6]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 12795051HCID 12795051, compound

Product 1

HCID 12795068HCID 12795068, compound

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

A solution of 17 g. of methyl N-(3-iodopropyl)-3-carbomethoxypyrrole-2-acetate is added portionwise over an hour to a stirred suspension of 52.7 g. (99%) NaH in 300 ml. dry dimethylformamide at 0° C. and maintained in nitrogen. The temperature is allowed to reach 20° and stirring is continued for 1 hour. The reaction mixture is diluted with saturated NaCl and extracted with benzene 4 times. The combined extracts are washed with water, dried over sodium sulfate and evaporated to dryness in vacuo. Recrystallization of the residue using benzene-hexane affords dimethyl 5,6,7,8-tetrahydropyrrolo[1,2-a]-pyridine-1,8-dicarboxylate (VII, R=H, n=1) m.p. 108° C.

Workup

  1. customto reach 20°
  2. extractionextracted with benzene 4 times
  3. washThe combined extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness in vacuo
  6. customRecrystallization of the residue

Sources & evidence

ORD record
ord-b31316a6b40847bebe2f8866e11580a6
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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