HCID 19899116, compound → HCID 19899111, compound

HRID 1196670Notes

Reaction equation

HRID 1196670 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]3[CH2:14][CH2:15][CH2:16][CH:17]([C:19]([O:21]C)=[O:20])[CH2:18][C:12]3(N3CCCC3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]>O.S(=O)(=O)(O)O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]3[CH2:14][CH2:15][CH2:16][CH:17]([C:19]([OH:21])=[O:20])[CH2:18][C:12]=3[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 1

HCID 19899116HCID 19899116, compound

Product 1

HCID 19899111HCID 19899111, compoundYield 17.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

5 g (0.012 mol) of methyl 3-(3,4-dichlorophenyl)-3a,5,6,7,8,8a-hexahydro-8a-pyrrolidino-4H-cyclohept[d]isoxazole-7-carboxylate were dissolved in a mixture of 5 ml of water, 5 ml of concentrated sulfuric acid and 5 ml of glacial acetic acid and heated at 120° C. for 1.5 hours. The mixture was cooled, whereupon the crystals which formed were filtered off and washed firstly with glacial acetic acid and then with water. After drying in a vacuum and crystallization from methanol, there was obtained 0.7 g of 3-(3,4-dichlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-7-carboxylic acid of melting point 183°-185° C.

Workup

  1. temperatureThe mixture was cooled, whereupon the crystals which
  2. customformed
  3. filtrationwere filtered off
  4. washwashed firstly with glacial acetic acid
  5. dry with materialAfter drying in a vacuum and crystallization from methanol

Sources & evidence

ORD record
ord-5e27a207cf9b4acd96361d6da57531b3
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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