Ethylamine → HCID 12831232, compound

HRID 1446855Notes

Reaction equation

HRID 1446855 reaction equation
C1C2C(=CC=CC=2)C=CC=1C=CC(=O)CC(OC)=O.COC(OC)N(C)C.C(N)C.[CH2:31]([NH:33][CH:34]=[C:35]([C:40](=[O:53])[CH:41]=[CH:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)[C:36]([O:38]C)=[O:37])[CH3:32]>C1(C)C=CC=CC=1>[CH2:31]([N:33]1[C:42]([C:43]2[CH:52]=[CH:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=2)=[CH:41][C:40](=[O:53])[C:35]([C:36]([OH:38])=[O:37])=[CH:34]1)[CH3:32]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 78373Dimethylformamide dimethyl acetalHCID 54428813HCID 54428813, compoundHCID 178464211HCID 178464211, compound

Product 1

HCID 12831232HCID 12831232, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

9 G. of methyl 5-(2-naphthyl)-3-oxo-4-pentenoate and 4.7 g. of dimethylformamide dimethylacetal were dissolved in 100 ml. of toluene and stirred at 60° C. for 22 hours. After cooling, the reaction mixture was evaporated. There were obtained about 10 g. of a dark red, viscous oil, which was treated with a solution of 100 g. of ethylamine in 1 l. of toluene. The reaction mixture was stirred at room temperature for 20 hours, evaporated and the crude product was purified by column chromatography [silica gel, methylene chloride/methanol (19:1, v/v)]. After recrystallization from ether/pentane, there were obtained 6.0 g. (55%) of methyl 2-[(ethylamino)-methylene]-5-(2-naphthyl)-3-oxo-4-pentenoate in the form of light yellowish crystals, mp 80°-82° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. customThere were obtained about 10 g
  4. additionof a dark red, viscous oil, which was treated with a solution of 100 g
  5. customevaporated
  6. customthe crude product was purified by column chromatography [silica gel, methylene chloride/methanol (19:1
  7. customAfter recrystallization from ether/pentane
  8. customthere were obtained 6.0 g

Sources & evidence

ORD record
ord-9397415decf24af0bfcce36efe014677
Source dataset
uspto-grants-1982_02
Patent number
US04314063

Reaction notes

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