1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 54568569, compound

HRID 868094Notes

Reaction equation

HRID 868094 reaction equation
[C:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:22])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][N:11]2[CH2:15][CH3:16])=[CH:6][C:5]=1[F:23])(=[O:3])[CH3:2].C(O[CH:29](OC(C)(C)C)[N:30]([CH3:32])[CH3:31])(C)(C)C>CN(C)C=O>[CH3:29][N:30]([CH3:32])[CH:31]=[CH:2][C:1]([C:4]1[C:13]([F:14])=[C:12]2[C:7]([C:8](=[O:22])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][N:11]2[CH2:15][CH3:16])=[CH:6][C:5]=1[F:23])=[O:3]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 13772822HCID 13772822, compound

Product 1

HCID 54568569HCID 54568569, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5.00 g (15.5 mmol) of the ethyl 7-acetyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 65 ml of dimethylformamide was added 4.27 ml (1.3 eq) of bis t-butoxydimethylaminomethane. The mixture was taken to 55° C. overnight. The mixture was concentrated and the solids suspended in ethyl ether. Filtration gave 4.88 g of the ethyl 7-(2'-dimethylaminoethenyl)carbonyl-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, mp 175°-177° C.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationFiltration

Sources & evidence

ORD record
ord-9f9aeb75b7354246b38d793f559eb0f8
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

Loading…