Hydrochloric Acid → HCID 12291139, compound

HRID 1579066Notes

Reaction equation

HRID 1579066 reaction equation
[Cl:1]C1C=CC2C3N(C4C=CC=CC=4)N=C(C(O)=O)C=3CCC=2C=1.S(Cl)(Cl)=O.S(=O)=O.[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[C:43]3[N:42]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[N:41]=[C:40]([C:50]([O:52][CH2:53][CH2:54][N:55]([CH2:58][CH3:59])[CH2:56][CH3:57])=[O:51])[C:39]=3[CH2:38][CH2:37][C:36]=2[CH:60]=1.Cl>C(O)C.CC(O)C.CCOCC>[ClH:1].[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[C:43]3[N:42]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[N:41]=[C:40]([C:50]([O:52][CH2:53][CH2:54][N:55]([CH2:58][CH3:59])[CH2:56][CH3:57])=[O:51])[C:39]=3[CH2:38][CH2:37][C:36]=2[CH:60]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24386Thionyl ChlorideHCID 12291086HCID 12291086, compoundHCID 12291138HCID 12291138, compound

Product 1

HCID 12291139HCID 12291139, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 5 parts of 7-chloro-1-phenyl-4,5-dihydro-1H-benz[g]indazole-3-carboxylic acid and 50 parts of thionyl chloride is heated on a steam bath until evolution of sulfur dioxide ceases. The excess thionyl chloride is then removed under reduced pressure and 50 parts of benzene is added to the resulting residue. The benzene is then distilled off under reduced pressure and the new residue is dissolved in 50 parts of benzene and 5 parts 2-diethylaminoethanol is added with stirring. The mixture is allowed to become warm and it is allowed to stand for 1 hour. Excess 2-diethylaminoethanol is distilled off under reduced pressure and the residue is partitioned with dilute hydrochloric acid and ether. The aqueous layer is separated and washed twice with ether before it is made alkaline with dilute sodium hydroxide and extracted with ether. The resulting ether solution is dried over potassium carbonate and concentrated. The residue obtained is 2-diethylaminoethyl 7-chloro-1-phenyl-4,5-dihydro-1H-benz[g]indazole-3-carboxylate. It is dissolved in anhydrous ethanol and a slight excess of hydrogen chloride in 2-propanol is added. Anhydrous ether is then added until the mixture becomes tubid and it is then cooled. The crystals which form are separated by filtration and recrystallized from a mixture of anhydrous ethanol and anhydrous ether to give 2-diethylaminoethyl 7-chloro-1-phenyl-4,5-dihydro-1H-benz[g]indazole-3-carboxylate hydrochloride melting at about 190°-192°C. The free base of this compound has the following formula ##SPC5##

Workup

  1. customThe excess thionyl chloride is then removed under reduced pressure and 50 parts of benzene
  2. additionis added to the resulting residue
  3. distillationThe benzene is then distilled off under reduced pressure
  4. dissolutionthe new residue is dissolved in 50 parts of benzene and 5 parts 2-diethylaminoethanol
  5. additionis added
  6. temperatureto become warm
  7. distillationExcess 2-diethylaminoethanol is distilled off under reduced pressure
  8. customthe residue is partitioned with dilute hydrochloric acid and ether
  9. customThe aqueous layer is separated
  10. washwashed twice with ether before it
  11. extractionextracted with ether
  12. dry with materialThe resulting ether solution is dried over potassium carbonate
  13. concentrationconcentrated
  14. customThe residue obtained
  15. temperatureis then cooled
  16. customThe crystals which form are separated by filtration
  17. customrecrystallized from a mixture of anhydrous ethanol and anhydrous ether

Sources & evidence

ORD record
ord-2366b7f7969e4c138a6a88273a68d558
Source dataset
uspto-grants-1976_02
Patent number
US03940418

Reaction notes

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