Ammonia → Cyclohepta[b]pyrrole-5-carbaldehyde

HRID 4590Notes

Reaction equation

HRID 4590 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-efc6ced26c664eaca2e01d57ea29f564
Source dataset
uspto-grants-1988_02
Patent number
US04727060

Reaction notes

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