Hydrochloric Acid → HCID 15240193, compound

HRID 843298Notes

Reaction equation

HRID 843298 reaction equation
CN(C)C=O.[N+:6]([C:9]1[CH:30]=[CH:29][C:12]([CH:13]=[C:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH:18]=[CH:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)=[CH:11][CH:10]=1)([O-])=O.Cl.[OH-].[Na+]>[Cl-].[Na+].O>[NH2:6][C:9]1[CH:30]=[CH:29][C:12]([CH:13]=[C:14]2[C:15]3[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=3[CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]2=3)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 22617097HCID 22617097, compound

Product 1

HCID 15240193HCID 15240193, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

To 150 ml of N,N-dimethylformamide, were added 10.0 g (30.7 mmol) of the above 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene, 8.0 g (143 mmol) of reduced iron powder and 2.70 ml (30.6 mmol) of concentrated hydrochloric acid (d=1.18, 35%). The resulting mixture was heated to the inner temperature of about 70° C., and then heated and stirred for 3 hours at the same temperature. After the reaction was completed, the reaction mixture was cooled in an ice water bath, and about 12.4 ml of an aqueous 10% sodium hydroxide solution was added thereto, followed by stirring and thereafter suction filtration. The filtrate obtained was poured in about 1 liter of saturated brine, and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. To thus obtained residue was added methanol, and the crystals precipitated were collected by filtration. The crystals were then recrystallized from methanol to give 8.41 g of 5-(4-aminobenzylidene)-5H-dibenzo[a,d]cycloheptene. Yield: 92.7%; m.p.: 119 to 120.0° C.

Workup

  1. temperatureheated
  2. temperaturethe reaction mixture was cooled in an ice water bath
  3. stirringby stirring
  4. filtrationsuction filtration
  5. customThe filtrate obtained
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. additionTo thus obtained residue was added methanol
  10. customthe crystals precipitated
  11. filtrationwere collected by filtration
  12. customThe crystals were then recrystallized from methanol

Sources & evidence

ORD record
ord-f7abc750d897443d8db66d7c7f66fa27
Source dataset
uspto-grants-2002_04
Patent number
US06376695B1

Reaction notes

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