Acetic Acid → HCID 20309098, compound

HRID 1763210Notes

Reaction equation

HRID 1763210 reaction equation
[C:1]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=O)([O:3]CC)=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[C:17]([F:23])[CH:16]=1.C1(C)C=CC=CC=1.C(O)(=O)C>O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:1](=[O:3])[C:6]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]=3[NH:22]2)=[C:17]([F:23])[CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 279795ethyl 2-oxocycloheptanecarboxylateHCID 2782934(4-Chloro-2-fluorophenyl)hydrazine

Product 1

HCID 20309098HCID 20309098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.3 parts of 2-carbethoxycycloheptanone [prepared by the method of G. Stork, et al., J. Am. Chem. Soc., 85, 207 (1963)], 8.1 parts of 4-chloro-2-fluorophenyl hydrazine, 100 parts of toluene and 0.5 parts of acetic acid was refluxed for 4 hours until all water was evolved. The resulting solution was cooled to -50° and filtered to yield 12 parts of 2-(4-chloro-2-fluorophenyl)-1,4,5,6,7,8-hexahydrocycloheptapyrazol-3(2H)-one melting at 197°-201°. Four parts of the pyrazolone was mixed with 4.4 parts of phosphorous oxybromide and 2.2 parts of N,N-diethylaniline in 200 parts of xylene and the mixture refluxed for 3 hours. 0.5 Part of N,N-dimethyl formamide was added and the mixture refluxed for 1 hour. The mixture was poured over 100 parts of ice and the phases separated. The organic phase was evaporated under reduced pressure of 50 mm. Hg at 70° to a crude product. The product was dissolved in 100 parts of chloroform, washed with 100 parts of 10% aqueous sodium carbonate, dried with anhydrous magnesium sulfate and evaporated to an oil under reduced pressure of 500 mm. Hg at 40°. Purification by chromatography on alumina using 3% ether in hexane as the eluent gave 0.8 parts of 3-bromo-2-(4-chloro-2-fluorophenyl)-2,4,5,6,7,8-hexahydrocycloheptapyrazole melting at 59°-60°.

Workup

  1. customprepared by the method of G
  2. temperatureThe resulting solution was cooled to -50°
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2498400f58a44806b27b6f0825ecd0ae
Source dataset
uspto-grants-1978_09
Patent number
US04111681

Reaction notes

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