Ethanol → HCID 178476575, compound

HRID 2165546Notes

Reaction equation

HRID 2165546 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH2:12])=[CH:9][CH:8]=[C:7]([F:13])[CH:6]=2.[Cl:14][C:15]([Cl:21])([Cl:20])[C:16](=[NH:19])[O:17]C.[CH2:22]([OH:24])[CH3:23]>C(O)(=O)C>[C:16]([OH:17])(=[O:24])[CH3:15].[C:22]([OH:17])(=[O:24])[CH3:23].[NH2:12][C:11]1[C:10]2[C:5](=[CH:6][C:7]([F:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:16](=[NH:19])[C:15]([Cl:21])([Cl:20])[Cl:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 100479Methyl 2,2,2-trichloroacetimidateHCID 10654878HCID 10654878, compound

Product 1

HCID 178476575HCID 178476575, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.77 g of 3,4-diamino-7-fluoro-quinoline (V-4) in 20 ml of acetic acid was added 1.94 g of methyl trichloroacetimidate and the mixture was stirred for two hours at room temperature. After concentration under reduced pressure, 10 ml of ethyl acetate was added to the residue, and the mixture was allowed to stand overnight. The crystals precipitated were collected by filtration and washed with ethyl acetate and then a small quantity of ethanol to give 3.75 g (yield: 87%) of the titled compound (VIII-1).

Workup

  1. concentrationAfter concentration under reduced pressure, 10 ml of ethyl acetate
  2. additionwas added to the residue
  3. waitto stand overnight
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-198e702fc4d84d86b5da4b6054943d45
Source dataset
uspto-grants-1990_07
Patent number
US04940714

Reaction notes

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