Pyridine → HCID 23456200, compound

HRID 866346Notes

Reaction equation

HRID 866346 reaction equation
[C:1]1([N:7]2[C:11]([CH:12]=[O:13])=[C:10]3[C:14]([CH3:21])([C:19]#[N:20])[CH2:15][C:16]([CH3:18])([CH3:17])[C:9]3=[C:8]2[CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mn]([O-])(=O)(=O)=[O:24].[K+].N1C=CC=CC=1>O>[C:1]1([N:7]2[C:11]([C:12]([OH:24])=[O:13])=[C:10]3[C:14]([CH3:21])([C:19]#[N:20])[CH2:15][C:16]([CH3:17])([CH3:18])[C:9]3=[C:8]2[CH3:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 516875Potassium PermanganateHCID 12607167HCID 12607167, compound

Product 1

HCID 23456200HCID 23456200, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following a procedure similar to that described in Example 13C, 17.48 g. (0.06 mole) of 2-phenyl-3-formyl-2,4,5,6-tetrahydro-1,4,6,6-tetramethylcyclopenta[c]pyrrole-4-carbonitrile was oxidized with 18.9 g. (0.12 mole) of potassium permanganate in 120 ml. of pyridine and 90 ml. of water to give 4.03 o 2-phenyl-3-carboxy-2,4,5,6-tetrahydro-1,4,6,6-tetramethylcyclopenta[c]pyrrole-4-carbonitrile which was esterified by reaction of 9.83 g. (0.032 mole) of the acid with 1.713 g. (0.035 mole) of a 50% mineral oil dispersion of sodium hydride followed by 2.23 ml (0.036 mole) of methyl iodide. There was thus obtained 4.18 g. of 2-phenyl-3-carbomethoxy-2,4,5,6-tetrahydro-1,4,6,6-tetramethylcyclopenta[c]pyrrole-4-carbonitrile.

Sources & evidence

ORD record
ord-fb10e78e089744588caa60d2dc4486b5
Source dataset
uspto-grants-1978_07
Patent number
US04098797

Reaction notes

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