Trifluoroacetic acid → [5-(4-Chlorobenzoyl)-4-methoxy-1-methyl-1H-pyrrol-2-yl]acetic acid

HRID 1388917Notes

Reaction equation

HRID 1388917 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[C:10](C(O)=O)[C:9]=2[O:21][CH3:22])=[O:7])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[O:21][CH3:22])=[O:7])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 204691265-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid

Product 1

HCID 13345722[5-(4-Chlorobenzoyl)-4-methoxy-1-methyl-1H-pyrrol-2-yl]acetic acid

Procedure

According to scheme (b), the precursor of formula IIb is decarboxylated under acidic, mild conditions. For example, 5-(p-chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid or its corresponding di(t-butyl) ester is treated with refluxing trifluoroacetic acid to afford 5-(p-chlorobenzoyl)-4-methoxy-1-methylpyrrole-2-acetic acid. Other acids may also be used. For example, those listed below in Table III.

Sources & evidence

ORD record
ord-7c4f6bfbd3354ce2a62d5dceb68d0174
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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