Potassium Carbonate → HCID 20071620, compound

HRID 981204Notes

Reaction equation

HRID 981204 reaction equation
[Cl:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[C:6]([CH:21]=1)=[N:7][C:8]1[NH:9][CH:10]=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([O:31][CH2:32]Cl)[CH3:30]>CN(C)C=O>[Cl:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[C:6]([CH:21]=1)=[N:7][C:8]1[N:9]([CH2:32][O:31][CH2:29][CH3:30])[CH:10]=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 20071616HCID 20071616, compound

Product 1

HCID 20071620HCID 20071620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

A suspension of 6 g of 8-chloro-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine and 5.16 g of potassium carbonate in 120 cm3 of dimethylformamide is heated at a temperature close to 110° C. for 1 hour. After cooling to about 15° C., 5.44 cm3 of chloromethyl ethyl ether are added and the mixture is stirred for 5 hours at between 15° and 20° C. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at about 60° C. The residue is taken up in 3 times 150 cm3 of trichloromethane. The combined organic extracts are filtered in order to remove the insoluble matter. The filtrate is dried over magnesium sulphate and concentrated under reduced pressure (20 kPa) at about 40° C. The residue is recrystallized from 55 cm3 of dimethylformamide. 5.6 g of 8-chloro-3 -ethoxycarbonyl-1-ethoxymethyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a beige solid melting at 261° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 110° C. for 1 hour
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at about 60° C
  4. filtrationThe combined organic extracts are filtered in order
  5. customto remove the insoluble matter
  6. dry with materialThe filtrate is dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure (20 kPa) at about 40° C
  8. customThe residue is recrystallized from 55 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-7318ce8c7a7a465eabc8d6a57d1cc346
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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