2-Bromoethanol → HCID 21435044, compound

HRID 267513Notes

Reaction equation

HRID 267513 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 crystallised 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. customcrystallised from ethanol, m.p. 219.5°-220° (24 %)

Sources & evidence

ORD record
ord-5f03504dc1524763969cbf172e8e8063
Source dataset
uspto-grants-1976_03
Patent number
US03943141

Reaction notes

Loading…