Sulfuric Acid → 1,3,5-trimethyl-N-(1,1,3-trimethyl-4-indanyl)pyrazole-4-carboxamide

HRID 1252169Notes

Reaction equation

S(=O)(=O)(O)O.[CH3:6][N:7]1[C:11]([CH3:12])=[C:10]([C:13]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]([CH3:25])[CH2:17][C:16]2([CH3:27])[CH3:26])=[O:14])[C:9]([CH3:28])=[N:8]1>>[CH3:6][N:7]1[C:11]([CH3:12])=[C:10]([C:13]([NH:15][C:24]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:19]=2[CH:18]([CH3:25])[CH2:17][C:16]3([CH3:26])[CH3:27])=[O:14])[C:9]([CH3:28])=[N:8]1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 20141121N-(1,3,5-trimethylpyrazole-4-yl carbonyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 141278841,3,5-trimethyl-N-(1,1,3-trimethyl-4-indanyl)pyrazole-4-carboxamideYield 54.8%

Procedure

5 cc of 85% aqueous sulfuric acid was added to 0.31 g of N-(1,3,5-trimethylpyrazole-4-yl carbonyl)-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline at room temperature, followed by stirring at the same temperature for 24 hours. The reaction mixture was poured into ice water. The precipitated crystal was filtered and washed with n-hexane. After being dried, the crystal was recrystallized from n-hexane-ethyl acetate to obtain 0.17 g of the objective 1,3,5-trimethyl-N-(1,1,3-trimethylindane-4-yl)pyrazole-4-carboxamide.

Workup

filtrationThe precipitated crystal was filtered
washwashed with n-hexane
customAfter being dried
customthe crystal was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-26c65718bea14d02beab0f4bbb3d320e
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04742074

Reaction notes

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