1,1-Dimethoxyethyl(dimethyl)amine → HCID 53773844, compound

HRID 1032727Notes

Reaction equation

HRID 1032727 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:21])[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[C:24](OC)([N:26]([CH3:28])[CH3:27])[CH3:25]>CN(C=O)C>[CH3:27][N:26]([CH3:28])[C:24]([CH3:25])=[CH:2][C:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:21])[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 14023624HCID 14023624, compound

Product 1

HCID 53773844HCID 53773844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 32.6 g ethyl 7-acetyl-1,4-dihydro1-ethyl-4-oxo-3-quinolinecarboxylate, 24 ml dimethylacetamide dimethylacetal and 100 ml DMF was heated on a steam bath for 4 hrs. The reaction mixture was concentrated in vacuo and the solid residue triturated with ethyl acetate. The solid product was recrystallized from acetonitrile to give 20.9 g ethyl 7-[3-(dimethylamino)-1-oxo2-butenyl]-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate, yellowish-orange powder, m.p. 178-179.5° C.

Workup

  1. temperaturewas heated on a steam bath for 4 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe solid residue triturated with ethyl acetate
  4. customThe solid product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-78bb26b44b2248ff88b6d130ffd6d31a
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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