Hydrochloric Acid → HCID 23133278, compound

HRID 1988115Notes

Reaction equation

HRID 1988115 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][N:4]([CH2:13][CH2:14][CH2:15][N:16]2C(=O)C4C(=CC=CC=4)C2=O)[CH:3]3[CH2:2]1.O.NN.[ClH:30]>C(O)C>[ClH:30].[ClH:30].[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][N:4]([CH2:13][CH2:14][CH2:15][NH2:16])[CH:3]3[CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 23133279HCID 23133279, compound

Product 1

HCID 23133278HCID 23133278, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-[3-(2,2a,4,5-Tetrahydro-1H-3-aza-acenaphthylen-3-yl)-propyl]-isoindole1,3-dione (2 g, 5.78 mmol) and hydrazine hydrate (2.9 g, 57.8 mol) in ethanol (60 mL) was refluxed for 1 h. The reaction mixture was cooled down and treated with an additional amount of ethanol (30 mL) and concentrated HCl (7 mL). Then the reaction mixture was refluxed for 4 h and left overnight in a refrigerator. The precipitate was filtered off, and the solvent was evaporated. The residue was redissolved in water (15 ml) and made alkaline with 25% ammonia. Then, was extracted with CH2Cl2 (3×120 mL), the organic layer was dried over Na2SO4, and evaporated to dryness. The crude was dissolved in ethylacetate. A 2.8 M solution of hydrogen chloride in ethanol was then added. The precipitate formed was collected by filtration to give the desired product (0.80 g, 64% yield) as a beige solid.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. temperatureThen the reaction mixture was refluxed for 4 h
  3. filtrationThe precipitate was filtered off
  4. customthe solvent was evaporated
  5. dissolutionThe residue was redissolved in water (15 ml)
  6. extractionThen, was extracted with CH2Cl2 (3×120 mL)
  7. dry with materialthe organic layer was dried over Na2SO4
  8. customevaporated to dryness
  9. dissolutionThe crude was dissolved in ethylacetate
  10. additionA 2.8 M solution of hydrogen chloride in ethanol was then added
  11. customThe precipitate formed
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f2858f91b1e94d5088b2b31d906d3906
Source dataset
uspto-grants-2009_06
Patent number
US07553965B2

Reaction notes

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