2-Bromoethanol → HCID 21435044, compound

HRID 2398245Notes

Reaction equation

HRID 2398245 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:19])[C:9]([C:14]([O:16]CC)=[O:15])=[CH:10][NH:11]2)=[CH:6][CH:5]=1)[CH3:2].Br[CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:19])[C:9]([C:14]([OH:16])=[O:15])=[CH:10][N:11]2[CH2:21][CH2:22][OH:23])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 23198586HCID 23198586, compound

Product 1

HCID 21435044HCID 21435044, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Ethoxy-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester (3.6 g), 2-bromoethanol and potassium carbonate (7.5 g) in dimethylformamide (50 ml) (4.95 ml) were stirred and heated on a steam bath for 16 hours. The solid was filtered off and the filtrate evaporated. The residue was crystallized from dimethylformamide. This ester (2.0 g) and aqueous sodium hydroxide (40 ml, 2N) were heated on a steam bath for 3 hours, cooled and acidified to pH 2 with aqueous hydrochloric acid. The solid was collected and crystallized from ethanol, m.p. 219.5°-220° (24%).

Workup

  1. temperatureheated on a steam bath for 16 hours
  2. filtrationThe solid was filtered off
  3. customthe filtrate evaporated
  4. customThe residue was crystallized from dimethylformamide
  5. temperatureThis ester (2.0 g) and aqueous sodium hydroxide (40 ml, 2N) were heated on a steam bath for 3 hours
  6. temperaturecooled
  7. customThe solid was collected
  8. customcrystallized from ethanol, m.p. 219.5°-220° (24%)

Sources & evidence

ORD record
ord-aec6c64c699b487e94b99757ce8eb191
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Reaction notes

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