Dimethylformamide → HCID 54112822, compound

HRID 259240Notes

Reaction equation

HRID 259240 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:19]([OH:21])=[O:20])=[CH:8][N:9]3[CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=2[O:2]1.CN(C)C=O.[CH3:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33]Cl)=[O:31]>C(N(CC)CC)C>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:19]([O:21][CH2:33][O:32][C:30](=[O:31])[C:29]([CH3:36])([CH3:35])[CH3:28])=[O:20])=[CH:8][N:9]3[CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 87885Chloromethyl pivalateHCID 20356988HCID 20356988, compound

Product 1

HCID 54112822HCID 54112822, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 2.6 g. 6,7-methylenedioxy-1-(2,2,2-trifluoroethyl)-4(1H)-quinolone-3-carboxylic acid and 35 ml. of dimethyl formamide was added 1.4 g. of triethylamine. The mixture was warmed to 55° and kept there for 1/2 hour. 2.8 g. of chloromethyl trimethylacetate was then added and the resulting mixture was stirred at 55° for 5 hours. The cooled solution was diluted with 150 ml. of ethyl acetate and washed with water. The ethyl acetate solution was dried over magnesium sulfate and concentrated. The solid residue, 6,7-methylenedioxy-1-(2,2,2-trifluoroethyl)-4(1H)-quinolone-3-carboxylic acid, trimethylacetoxymethyl ester, was recrystallized from CH2Cl2 -ether mixture; m.p. 190°-1°.

Workup

  1. additionTo a mixture of 2.6 g
  2. temperatureThe mixture was warmed to 55°
  3. additionThe cooled solution was diluted with 150 ml
  4. washof ethyl acetate and washed with water
  5. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe solid residue, 6,7-methylenedioxy-1-(2,2,2-trifluoroethyl)-4(1H)-quinolone-3-carboxylic acid, trimethylacetoxymethyl ester, was recrystallized from CH2Cl2 -ether mixture

Sources & evidence

ORD record
ord-cb4dda06b037417f9dedbedae2aefec4
Source dataset
uspto-grants-1977_07
Patent number
US04036962

Reaction notes

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