Methyl acetoacetate → ST50708819

HRID 2254130Notes

Reaction equation

HRID 2254130 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:13]([O:19][CH3:20])(=[O:18])[CH2:14][C:15]([CH3:17])=O.Cl.[CH3:22][NH2:23]>N1C=CC=CC=1>[CH3:22][N:23]1[C:15]([CH3:17])=[C:14]([C:13]([O:19][CH3:20])=[O:18])[CH:7]([C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)[C:14]([C:13]([O:19][CH3:20])=[O:18])=[C:15]1[CH3:17]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 679964-(Trifluoromethyl)benzaldehydeHCID 6364545Methylamine hydrochloride

Product 1

HCID 2167221ST50708819

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5.22 g (0.03 mol) of 4-trifluoromethylbenzaldehyde, 7.04 g (0.06 mol) of methyl acetoacetate and 2.07 g (0.03 mol) of methylamine hydrochloride in 20 ml of pyridine is stirred under reflux for 5 hours. After removing the pyridine by distillation, the mixture is partitioned between water and methylene chloride, and the organic phase is washed with water, dried over sodium sulphate and evaporated. The residue is recrystallized from methanol.

Workup

  1. temperatureunder reflux for 5 hours
  2. customAfter removing the pyridine
  3. distillationby distillation
  4. customthe mixture is partitioned between water and methylene chloride
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-ded9fdedfd2c4523ba39bc8f6b90dfed
Source dataset
uspto-grants-1993_08
Patent number
US05234935

Reaction notes

Loading…