Potassium Cyanide → HCID 23456202, compound

HRID 866344Notes

Reaction equation

HRID 866344 reaction equation
[H][H].O=C1C2C(=[C:8](C)[N:9](C)C=2C)CC1.C[Mg]Br.O[C:19]1([CH3:30])[C:26]2[C:22](=[C:23]([CH3:29])[N:24]([CH3:28])[C:25]=2[CH3:27])[CH2:21][CH2:20]1.[C-]#N.[K+].C([O-])(=O)C.[K+]>[Pd].C(O)(=O)C>[CH3:29][C:23]1[N:24]([CH3:28])[C:25]([CH3:27])=[C:26]2[C:19]([CH3:30])([C:8]#[N:9])[CH2:20][CH2:21][C:22]=12

Participants

9

Reactant 6

HCID 9032Potassium CyanideHCID 517044Potassium AcetateHCID 23456179HCID 23456179, compoundHCID 23456207HCID 23456207, compoundHCID 178418361HCID 178418361, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 23456202HCID 23456202, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Reduction of the latter with hydrogen over a palladium-on-charcoal catalyst; alkaline saponification of the resulting 3-(1,2,5-trimethyl-3-pyrrole) propionitrile; cyclization of the resulting 3-(1,2,5-trimethyl-3-pyrrole)propionic acid with polyphosphoric acid; reaction of the resulting 4-oxo-1,2,3-trimethyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole with methyl magnesium bromide; and reaction of the resulting 4-hydroxy-1,2,3,4-tetramethyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole with potassium cyanide and potassium acetate in glacial acetic acid using the procedure described above in Example 10 affords 1,2,3,4-tetramethyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitrile.

Sources & evidence

ORD record
ord-2eb0e42eb8e1402a8ce19ab3d026fc24
Source dataset
uspto-grants-1978_07
Patent number
US04098797

Reaction notes

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