1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → 7-(2'-Dimethylaminoethenyl)carbonyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester

HRID 622529Notes

Reaction equation

HRID 622529 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][C:5]=1[F:22])(=[O:3])[CH3:2].C(O[CH:28](OC(C)(C)C)[N:29]([CH3:31])[CH3:30])(C)(C)C>CN(C)C=O>[CH2:19]([O:18][C:16]([C:9]1[C:8](=[O:21])[C:7]2[C:12](=[CH:13][C:4]([C:1]([CH:2]=[CH:28][N:29]([CH3:31])[CH3:30])=[O:3])=[C:5]([F:22])[CH:6]=2)[N:11]([CH2:14][CH3:15])[CH:10]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 13772817Ethyl 7-acetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 540574497-(2'-Dimethylaminoethenyl)carbonyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To 2.0 (6.5 mmol) of ethyl 7-acetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 50 ml of dimethylformamide was added 1.71 ml (1.25 eq) of bis-t-butoxydimethylaminomethane. The mixture was heated at 70° C. for 18 hours. The mixture was then concentrated and the residue treated with ether and filtered to give 1.95 g of 7-(2'-dimethylaminoethenyl)carbonyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester, mp 176°-179° C.

Workup

  1. concentrationThe mixture was then concentrated
  2. additionthe residue treated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-57176cf5e7f94668a46d269e9c267039
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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