2,6-Dimethylaniline → HCID 12788130, compound

HRID 745309Notes

Reaction equation

HRID 745309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16](Cl)=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2.[CH3:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:23]=1[NH2:24].C1C=CC=CC=1.C(OCC)(=O)C>C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16]([NH:24][C:23]3[C:25]([CH3:29])=[CH:26][CH:27]=[CH:28][C:22]=3[CH3:21])=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 46787202-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-oneHCID 21583983Benzene ethyl acetate

Product 1

HCID 12788130HCID 12788130, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 9,10-dimethoxy-2-chloro-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one (2.5 g), 2,6-dimethylaniline (5.0 ml) in butanol (20.0 ml) is heated under reflux for 10 hours. The solvent is evaporated under reduced pressure to give a gummy mass. Chromatography of the gummy mass over silica gel using benzene-ethyl acetate as the eluant gives the required product. The compound is crystallized from methanol, yield 2.0 g, m.p. 297°-299° C.

Workup

  1. temperatureunder reflux for 10 hours
  2. customThe solvent is evaporated under reduced pressure
  3. customto give a gummy mass

Sources & evidence

ORD record
ord-f2639135826f4269a72bc2fe79639dfe
Source dataset
uspto-grants-1986_07
Patent number
US04598148

Reaction notes

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