Ammonia → Cyclohepta[b]pyrrole-5-carbaldehyde

HRID 2106962Notes

Reaction equation

HRID 2106962 reaction equation
[N:1]1[CH:5]=[CH:4][C:3]2=[CH:6][CH:7]=[CH:8][CH:9]=[CH:10][C:2]=12.C(Cl)(=O)[C:12](Cl)=[O:13].C([O-])(=O)C.[Na+].N>CN(C=O)C>[N:1]1[CH:5]=[CH:4][C:3]2=[CH:6][C:7]([CH:12]=[O:13])=[CH:8][CH:9]=[CH:10][C:2]=12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 517045Sodium AcetateHCID 13805010Cyclohepta[b]pyrrole

Product 1

HCID 23049656Cyclohepta[b]pyrrole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclohepta[b]pyrrole-5-carboxylic acid nitrile: 800 mg of cyclohepta[b]pyrrole (manufactured according to Helv. Chim. Acta 67, 1647 (1984)) are added in portions, at 0°, to a solution of 1.1 ml of oxalyl chloride in 40 ml of DMF. The whole is subsequently stirred for 30 minutes at room temperature, then 60 ml of saturated sodium acetate solution are added and the pH is adjusted to 9 with concentrated ammonia. The cyclohepta[b]pyrrole-5-carbaldehyde formed is extracted with methylene chloride and purified by flash chromatography with solvent system N6. Rf (N6)=0.46.

Sources & evidence

ORD record
ord-8065eec39272499ebfc73d9d5cf21c40
Source dataset
uspto-grants-1990_06
Patent number
US04931591

Reaction notes

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