N-Ethylaniline → HCID 54678936, compound

HRID 1421492Notes

Reaction equation

HRID 1421492 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Br:12])[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]([OH:17])=O.C(N(CC)CC)C.[CH2:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:26].S(Cl)(Cl)=O>ClCCl>[CH2:25]([N:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]([C:3]1[C:4](=[O:14])[N:5]([CH3:13])[C:6]2[C:11]([C:2]=1[OH:1])=[C:10]([Br:12])[CH:9]=[CH:8][CH:7]=2)=[O:17])[CH3:26]

Participants

6

Reactant 4

HCID 7670N-EthylanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 547078345-Bromo-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid

Product 1

HCID 54678936HCID 54678936, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of 1,2-dihydro-4-hydroxy-5-bromo-1-methyl-2-oxo-quinoline-3-carboxylic acid (9.6 g, 0.032 mol), triethylamine (15.5 ml, 0.11 mol) and N-ethylaniline (4.2 g, 0.035 mol) in 150 ml of dichloromethane was added dropwise during 0.5 hours a solution of thionyl chloride (3.0 ml, 0.042 mol) in 10 ml of dichloromethane. The stirring was continued at 4° C. for 24 hours. The solvents were evaporated. The residue was dissolved in ethyl acetate, filtered through celite and extracted with 2 M sodium hydroxide. The aqueous phase was washed with ethyl acetate and then acidified with hydrochloric acid to pH 5. On standing a crystalline precipitate was formed which was filtered off, washed with water and dried to give the title compound (8.5 g), yield 69%.

Workup

  1. customThe solvents were evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. filtrationfiltered through celite
  4. extractionextracted with 2 M sodium hydroxide
  5. washThe aqueous phase was washed with ethyl acetate
  6. customwas formed which
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-50a8f99ded684bcfb53b1fbe0f5433ee
Source dataset
uspto-grants-2000_06
Patent number
US06077851

Reaction notes

Loading…