Hydrochloric Acid → HCID 19439673, compound

HRID 1734018Notes

Reaction equation

HRID 1734018 reaction equation
O.NN.[C:4]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[CH2:9][N:10]1C(=O)C2=CC=CC=[C:12]2[C:11]1=[O:20])#[N:5].Cl>CO.O1CCCC1>[C:4]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[CH2:9][NH:10][C:11](=[O:20])[CH3:12])#[N:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 123753363-((1,3-Dioxoisoindolin-2-yl)methyl)benzonitrile

Product 1

HCID 19439673HCID 19439673, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydrazine hydrate (4.0 g) in methanol was added dropwise to a mixture of N-(3-cyanobenzyl)phthalimide (17.0 g) in tetrahydrofuran (150 ml) and methanol (120 ml) at ambient temperature under stirring and the resultant mixture was stirred for 3 hours at ambient temperature. To the reaction mixture was added dropwise 6N-hydrochloric acid (25 ml) and the mixture was stirred for one hour at ambient temperature. The reaction mixture was evaporated in vacuo. To the residue was added water (60 ml) and the mixture was stirred at 10 minutes and filtrated. The filtrate was washed with ethyl acetate and adjusted to pH 8.0 with 20% potassium carbonate solution. Acetic anhydride (15 ml) was added dropwise to the resulting solution at 8° to 20° C. under stirring and the mixture was stirred for one hour at 10° to 20° C. The reaction mixture was extracted with ethyl acetate, and extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give N-(3-cyanobenzyl)acetamide (7.45 g).

Workup

  1. stirringthe mixture was stirred for one hour at ambient temperature
  2. customThe reaction mixture was evaporated in vacuo
  3. additionTo the residue was added water (60 ml)
  4. stirringthe mixture was stirred at 10 minutes
  5. filtrationfiltrated
  6. washThe filtrate was washed with ethyl acetate
  7. additionAcetic anhydride (15 ml) was added dropwise to the resulting solution at 8° to 20° C.
  8. stirringunder stirring
  9. stirringthe mixture was stirred for one hour at 10° to 20° C
  10. extractionThe reaction mixture was extracted with ethyl acetate
  11. extractionextract
  12. washwas washed with brine
  13. dry with materialdried over magnesium sulfate
  14. customThe solvent was evaporated in vacuo
  15. customthe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-58480338e0874a3b81c5d0453c97a24e
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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