42779-82-8 Usage
Originator
Nidran Cont. ,Pharma
Uses
Anti-inflammatory.
Manufacturing Process
2 Methods of producing of 1-p-chlorophenyl-2,5-dimethyl-3-pyrroleacetic acid
1. To 47.0 g (0.23 mol) of finely ground 1-p-chlorophenyl-2,5-dimethylpyrrole,
a solution of 47.5 ml of an aqueous solution of 40% dimethylamine, 57.5 ml
of acetic acid and 27.5 ml of 35% formaldehyde is slowly added while stirring.
The mixture is stirred overnight at room temperature and extraction is made
with 2 x 100 ml of ether. To the aqueous phase, 700 ml of 20% NaOH are
added and extraction is made with ether. The organic phase is dried on
MgSO4, filtered and evaporated. To the residue obtained, 60 ml of absolute
ethanol are added, then dropwise while stirring 34.1 g of methyl iodide. The
mixture is stirred for 1 h, then the precipitate obtained is filtered; 85.9 g
(yield: 92.5%) of methiodide of 1-p-chlorophenyl-2,5-dimethyl-3-
dimethylaminomethylpyrrole are thus obtained, melting point 197°-201°C
(dec).
To 166.0 g (0.41 mol) of the methiodide of 1-p-chlorophenyl-2,5-dimethyl-3-
dimethylaminomethylpyrrole in 600 ml of dimethylsulfoxide, 66.6 g of sodium
cyanide are added and the mixture is heated to 100°C with stirring and under
a nitrogen stream for 3.5 h. After cooling, the mixture is poured into 1500 ml
of water and extracted with ether. The ethereal phase is washed with water,
dried on MgSO4 and evaporated. The residue is vacuum stripped; 62.1 g of a
yellow oil are thus obtained, which rapidly solidifies and which is recrystallized
from aqueous methanol, 57.4 g (yield: 56%) of 1-p-chlorophenyl-2,5-
dimethyl-3-pyrrole acetonitrile are obtained, melting point 86°-88°C, boiling
point 158°-161°C (0.4 mm).
To 64.0 g of 1-p-chlorophenyl-2,5-dimethyl-3-pyrrole acetonitrile, 64.0 g of
KOH and 300 ml of ethanol are added and the mixture is refluxed for 15 h.
The alcohol is evaporated and one dilutes with 300 ml of water. The aqueous
phase is washed with ether, and then acidified with 20% HCl. The precipitated
obtained is filtered and one washes with petroleum ether and a minimum of
ether. 58.5 g (yield: 85%) of 1-p-chlorophenyl-2,5-dimethyl-3-pyrroleacetic
acid are thus obtained, melting point 99.5°-101°C.2. To 9.5 g of 3-acetyl-2,5-hexanedione in 50 ml of benzene, 7.7 g of pchloroaniline are added and the mixture is refluxed for 5 h with azeotropi
removal of the water formed. The excess solvent is evaporated and residue is
vacuum stripped: 12.0 g (yield: 80%) of 1-p-chlorophenyl-2,5-dimethyl-3-
acetylpyrrole as an orange oil which rapidly crystallizes are thus obtained,
boiling point 144°-146°C. Melting point of it 80°-81°C (recrystallization from
hexane).
To 5.0 g of the 1-p-chlorophenyl-2,5-dimethyl-3-acetylpyrrole, 0.7 g of sulfur
and 2.7 ml of morpholine are added and the mixture is refluxed for 5 h. Then,
20 ml of an aqueous solution of 20% are added and the mixture is refluxed
for 4 h. The mixture is washed with ether, acidified with 20% HCl, and then
extracted with ether. The organic phase is extracted with a 10% sodium
bicarbonate solution which is acidified with 5% HCl. The solid obtained is
filtered and recrystallized several times from a diethyl ether-pentane mixture.
1.1 g (yield: 20%) of 1-p-chlorophenyl-2,5-dimethyl-3-pyrroleacetic acid are
thus obtained, melting point 100°-103°C.
Therapeutic Function
Antiinflammatory
Check Digit Verification of cas no
The CAS Registry Mumber 42779-82-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,7,7 and 9 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 42779-82:
(7*4)+(6*2)+(5*7)+(4*7)+(3*9)+(2*8)+(1*2)=148
148 % 10 = 8
So 42779-82-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H14ClNO2/c1-9-7-11(8-14(17)18)10(2)16(9)13-5-3-12(15)4-6-13/h3-7H,8H2,1-2H3,(H,17,18)/p-1
42779-82-8Relevant academic research and scientific papers
Derivatives of antiphlogistically effective carboxylic acids, their preparation and medicinal use
-
, (2008/06/13)
Compounds of Formula I STR1 wherein R1 is the residue of an antiphlogistically effective carboxylic acid of the formula R1 COOH, n is an integer 1, 2, or 3, and X is oxygen, sulfur, or optionally alkylated nitrogen have valuable antiinflammatory activity.
Esters and amides containing the 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl moiety
-
, (2008/06/13)
Compounds of the formula STR1 wherein each X, which may be identical or different from the other X, is oxygen or imino; R1 is hydrogen, fluorine, chlorine or bromine; R2 and R3, which may be identical or different from each other, are each hydrogen; unsubstituted or mono-substituted alkyl of 1 to 6 carbon atoms, where the substituent is phenyl or dialkylamino with 1 to 3 carbon atoms in each alkyl moiety; pyridyl; or cycloalkyl of 5 to 7 carbon atoms; R2 and R3, together with each other and the nitrogen atoms to which they are attached, are pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-aryl-piperazino or N-(alkyl of 1 to 3 carbon atoms)-piperazino; A is cycloalkylene of 5 to 7 carbon atoms; unsubstituted or substituted alkylene of 2 to 10 carbon atoms, where the substituents are one to two alkyls of 1 to 3 carbon atoms each, one to two carbalkoxys of 2 to 4 carbon atoms each, one to two phenyls, one to four hydroxyls, one halomethyl, one hydroxymethyl, one alkanoyloxy of 1 to 18 carbon atoms, one alkanoyloxymethyl of 1 to 18 carbon atoms in the alkanoyl moiety or one STR2 where R1, R2 and R3 have the meanings previously defined; or alkylene of 2 to 10 carbon atoms interrupted by oxygen, sulfur, sulfoxide, sulfonyl, phenyl, cyclohexyl, pyridyl, piperazino or unsubstituted or substituted imino, where the substituent on the imino group is alkyl of 1 to 6 carbon atoms, phenyl or phenylalkyl of 1 to 3 carbon atoms in the alkyl moiety; B is the acyl residue of an antiphlogistic carboxylic acid; and their non-toxic, pharmacologically acceptable acid addition salts. The compounds as well as their salts are useful as anti-inflammatories.
