Methanol → 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal semicarbazone

HRID 2072520Notes

Reaction equation

HRID 2072520 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:16])[CH:14]=O)=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2.CO.Cl.[NH2:24][NH:25][C:26]([NH2:28])=[O:27]>N1C=CC=CC=1.O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:16])[CH:14]=[N:24][NH:25][C:26]([NH2:28])=[O:27])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2

Participants

6

Reactant 3

HCID 887MethanolHCID 11236Semicarbazide hydrochlorideHCID 214093832-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

Product 1

HCID 541752422-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal semicarbazone

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 0.288 g. of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal in 3 ml. of methanol is added a solution of 0.111 g. of semicarbazide hydrochloride in 0.5 ml. of water, followed by 1 drop of pyridine. The mixture is refluxed briefly and then poured into water. The product is extracted with ethyl acetate and the extract washed, dried and evaporated to afford, upon crystallization from ethyl acetate/hexane, 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal semicarbazone.

Workup

  1. temperatureThe mixture is refluxed briefly
  2. extractionThe product is extracted with ethyl acetate
  3. washthe extract washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-18383c26125148a4b85391ea1cf9ba90
Source dataset
uspto-grants-1977_09
Patent number
US04051260

Reaction notes

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