Methylamine → HCID 22914835, compound

HRID 1377487Notes

Reaction equation

HRID 1377487 reaction equation
[CH3:1][NH2:2].CO[C:5](=[O:27])[CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11](=[O:19])[N:10]([CH3:20])[C:9]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C>ClCCl.CO>[CH3:1][NH:2][C:5](=[O:27])[CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11](=[O:19])[N:10]([CH3:20])[C:9]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 22914855HCID 22914855, compound

Product 1

HCID 22914835HCID 22914835, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stream of gaseous methylamine is passed into a 250 ml round-bottomed flask containing a solution of 1.7 g (4.78 mmol) of methyl7-chloro-2-methyl-1-oxo-3-phenyl-1,2-dihydroisoquinoline-4-propanoate in 20 ml of dichloromethane and 80 ml of methanol until saturation and the mixture is left stirring at room temperature for 4 days. The solvents are evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 80/20 and then with a 95/5 mixture of dichloromethane and methanol. After recrystallizing from ethyl acetate, 1.36 g (3.83 mmol) of white solid are obtained. Melting point: 161°-162° C.

Workup

  1. waitthe mixture is left
  2. customThe solvents are evaporated under reduced pressure
  3. customthe residue is purified by chromatography on a column of silica gel, elution
  4. additionbeing carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 80/20
  5. additionwith a 95/5 mixture of dichloromethane and methanol
  6. customare obtained

Sources & evidence

ORD record
ord-a46bc0efdeb041fd9cf3917a0d390f64
Source dataset
uspto-grants-1997_09
Patent number
US05665733

Reaction notes

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