Methyl Acrylate → HCID 70424265, compound

HRID 2308602Notes

Reaction equation

HRID 2308602 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:17][C@H:16]2[C@@H:6]([CH2:7][C:8]3[C:18]4[C:11](=[CH:12][CH:13]=[CH:14][C:15]2=4)[NH:10][CH:9]=3)[N:5]([CH3:19])[CH2:4]1.[C:20]([O:24][CH3:25])(=[O:23])[CH:21]=[CH2:22]>CO>[CH3:19][N:5]1[C@H:6]2[C@@H:16]([C:15]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:18]=3[C:8]([CH2:7]2)=[CH:9][NH:10]4)[CH2:17][C@@H:3]([CH2:2][NH:1][CH2:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])[CH2:4]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 10611049HCID 10611049, compound

Product 1

HCID 70424265HCID 70424265, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.1 g of 8β-aminomethyl-6-methyl-ergoline and 1.8 ml of methyl acrylate in 100 ml of methanol was refluxed for four hours. The solvent was evaporated off under reduced pressure, and the residue was crystallized from diethyl ether to give 6 g of 6-methyl-8β-[N-(2-methoxycarbonylethyl)-aminomethyl]-ergoline (II: R1 =R2 =R3 =R7 =R8 =H, R4 =CH3, n=1, A=CH2 --CHR6, R6 =H, B=COOCH3) melting at 130°-132° C. To a solution of 2.86 g of potassium cyanate in 30 ml of water, a solution of 6 g of 6-methyl-8β-[N-(2-methoxycarbonylethyl)-aminomethyl]-ergoline in 120 ml of water and 35 ml of 1N hydrochloric acid was added. This reaction mixture was heated for four hours at 80° C. and allowed to stand overnight at room temperature. The solid separated out and was filtered off and recrystallized from ethanol to give 4.5 g of the title compound melting at 330° C. with decomposition.

Workup

  1. temperaturewas refluxed for four hours
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-1d97748b06614015ba7872d2a8f8c454
Source dataset
uspto-grants-1987_09
Patent number
US04690929

Reaction notes

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