Sulfuric Acid → HCID 14099128, compound

HRID 358892Notes

Reaction equation

HRID 358892 reaction equation
[F:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[NH:5][CH2:6][CH3:7].C(O[CH:17]=[C:18]([C:24]([O:26]CC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>>[F:11][C:10]1[CH:9]=[C:8]2[C:4](=[C:3]([O:12][CH3:13])[C:2]=1[F:1])[N:5]([CH2:6][CH3:7])[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]2=[O:26]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 7918Acetic AnhydrideHCID 20067147HCID 20067147, compound

Product 1

HCID 14099128HCID 14099128, compoundYield 32%

Procedure

A mixture of 4.0 g (0.021 mole) of the 3,4-difluoro-N-ethyl-2-methoxyaniline (XIII) [prepared as described in Step (C3) above] and 5.54 g (0.026 mole) of diethyl ethoxymethylenemalonate was heated at 150°-160° C. for 9 hours. The mixture was then allowed to cool to room temperature, and 42 ml of acetic anhydride and 18 ml of concentrated sulfuric acid were then added, in that order. The reaction mixture was poured into ice-water to precipitate crystals, which were collected by filtration to give 2.09 g of ethyl 6,7-difluoro-1-ethyl-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (X, R9' =ethyl) as a colorless powder.

Workup

  1. temperaturewas heated at 150°-160° C. for 9 hours
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-5478bcdd7a9a4ad4892e8b6345c28dc9
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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