Ethanol → HCID 54461106, compound

HRID 616722Notes

Reaction equation

HRID 616722 reaction equation
[C:1]1([C:7]2[C:19]([C:20]([OH:22])=[O:21])=[C:10]3[C:11]4[C:16]([CH2:17][CH2:18][N:9]3[N:8]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.C(=O)(O)[O-].[Na+].[CH2:32](O)[CH3:33]>>[CH2:32]([O:21][C:20]([C:19]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=12)=[O:22])[CH3:33]

Participants

5

Reactant 4

HCID 702EthanolHCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 12948308HCID 12948308, compound

Product 1

HCID 54461106HCID 54461106, compound

Procedure

2-Phenyl-5,6-dihydro-pyrazolo[5,1-a]isoquinoline-1-carboxylic acid (7.48 g.) is stirred at 90° C. for three hours with 3.77 ml. of SOCl2. The thionyl chloride excess is eliminated in vacuo and the residual acid chloride is dissolved in 80 ml. of ethanol at 40°-50° C. After 15 minutes, the reaction mixture is neutralized by addition of aqueous sodium bicarbonate and the solvent is eliminated by distillation. The residue is extracted with ethyl ether and, after evaporation of the organic solution, is crystallized from isopropyl ether. Yield of title compound 2.47 g.; m.p. 84°-5° C.

Workup

  1. customat 40°-50° C
  2. distillationthe solvent is eliminated by distillation
  3. extractionThe residue is extracted with ethyl ether
  4. customafter evaporation of the organic solution
  5. customis crystallized from isopropyl ether

Sources & evidence

ORD record
ord-320aeeb2af37423dbca0ebc841aa7c77
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

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