1-methyl-1H-pyrrole-3-carboxylic acid → Methyl 1-methyl-5-cyclohexylcarbonylpyrrole-3-carboxylate

HRID 1703293Notes

Reaction equation

HRID 1703293 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:15])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10](Cl)[CH:9]=2)=[CH:5][C:4]([C:16]([O:18][CH3:19])=[O:17])=[CH:3]1.CN1C=CC(C(O)=O)=C1>>[CH3:1][N:2]1[C:6]([C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:15])=[CH:5][C:4]([C:16]([O:18][CH3:19])=[O:17])=[CH:3]1

Participants

3

Reactant 2

HCID 101540541-methyl-1H-pyrrole-3-carboxylic acidHCID 12783822HCID 12783822, compound

Product 1

HCID 20401039Methyl 1-methyl-5-cyclohexylcarbonylpyrrole-3-carboxylate

Procedure

Belgian patent 870,910 (published Mar. 29, 1979) discloses preparation of analogous 1-alkyl-5-acylpyrrole-3-carboxylates, specifically exemplifying preparation of methyl 1-methyl-5-(3-chlorobenzoyl)pyrrole-3-carboxylate by Friedel-Crafts acylation of 1-methylpyrrole-3-carboxylic acid followed by esterification and separation from the 4-acyl isomer.

Workup

  1. customfollowed by esterification and separation from the 4-acyl isomer

Sources & evidence

ORD record
ord-e8d6f388796349dabc312d472ec10a85
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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