Methyl acetoacetate → HCID 86714143, compound

HRID 919891Notes

Reaction equation

HRID 919891 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH3:11][O:12][C:13](=[O:18])[CH2:14][C:15](=O)[CH3:16].[CH3:19][O:20][C:21](=[O:24])[C:22]#[CH:23]>CO>[CH3:19][O:20][C:21](=[O:24])[CH:22]=[CH:23][C:14](=[C:15]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:16])[C:13]([O:12][CH3:11])=[O:18]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 13536Methyl propiolateHCID 754524-Methoxybenzylamine

Product 1

HCID 86714143HCID 86714143, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-methoxybenzyl amine (3 g, 21.9 mmol) and 3-oxo-butyric acid methyl ester (2.83 mL, 26.2 mmol) in MeOH (80 mL) was refluxed for 2 h. Propynoic acid methyl ester (2.92 mL, 32.8 mmol) was added, and the resulting mixture was refluxed for 48 h. After cooling to r.t., the solvent was evaporated, and the crude residue was recrystallized from MeOH to give 5 g of the title compound as a yellow solid. 1H NMR (CDCl3, 200 MHz): δ=10.87 (br s, 1H), 7.76 (d, 1H, J=15.4 Hz), 7.18 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.8 Hz), 6.09 (d, 1H, J=15.4 Hz), 4.50 (d, 2H, J=5.8 Hz), 3.80 (s, 3H), 3.77 (s, 3H), 3.73 (s, 3H), 2.27 (s, 3H).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe resulting mixture was refluxed for 48 h
  3. customthe solvent was evaporated
  4. customthe crude residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-f4a7907c59c7473b99921cabcd10146d
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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