Hydrochloric Acid → HCID 53966971, compound

HRID 1606126Notes

Reaction equation

HRID 1606126 reaction equation
[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[CH:17][CH2:18][CH2:19][N:20]3[C:24](=O)C4=CC=CC=C4[C:21]3=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.O.NN.Cl>C(O)C>[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[CH:17][CH2:18][CH2:19][N:20]([CH3:24])[CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 54052154HCID 54052154, compound

Product 1

HCID 53966971HCID 53966971, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.2 g. of 1-methyl-5-(3-phthalimidopropylidene)-5H-dibenzo [a,d]cycloheptene are dissolved in 100 ml. of ethanol, treated with 1.2 g. of hydrazine hydrate and heated for 6 hours under reflux conditions. An excess of concentrated hydrochloric acid is added, and the mixture is heated for an additional hour under reflux conditions. The reaction mixture is filtered warm. The solid residue is washed with warm ethanol, and the residual ethanol portions are evaporated to dryness. The residue is taken up in ether. The ethereal solution is washed with dilute sodium hydroxide solution, dried and evaporated whereby 1-methyl-5-(3-aminopropylidene)-5H-dibenzo[a,d]cycloheptene remains behind as a thick oil.

Workup

  1. temperaturethe mixture is heated for an additional hour under reflux conditions
  2. filtrationThe reaction mixture is filtered
  3. temperaturewarm
  4. washThe solid residue is washed with warm ethanol
  5. customthe residual ethanol portions are evaporated to dryness
  6. washThe ethereal solution is washed with dilute sodium hydroxide solution
  7. customdried
  8. customevaporated whereby 1-methyl-5-(3-aminopropylidene)-5H-dibenzo[a,d]cycloheptene

Sources & evidence

ORD record
ord-1b33b2fe0fbe4ea8abc711167b9dc1ae
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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