Potassium Carbonate → HCID 20461950, compound

HRID 326053Notes

Reaction equation

HRID 326053 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[N+:9]([C:12]1[C:13]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[N+:9]([C:12]1[C:13]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:25][CH:24]=2)=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13472703HCID 13472703, compound

Product 1

HCID 20461950HCID 20461950, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of ethyl 2-bromopropionate (0.5 g), 4-[N-(3-nitro-2-quinolinyl)amino]phenol (0.5 g), anhydrous potassium carbonate (0.3 g) and ethyl methyl ketone (20 ml) was refluxed for 4 hours. The solvent was removed under reduced pressure and the residue was partitioned between methylene chloride and water. The organic layer was dried and evaporated to give ethyl 2-{4-[N-(3-nitro-2-quinolinyl)amino]phenoxy}propionate as an orange oil which was purified by chromatography over silica gel. Proton magnetic resonance spectrum: (CDCl3, δ in ppm): 9.6 (1H, s, NH); 8.9 (1H, s, C4 quinoline proton); 7.8-7.6 (4H, m, quinoline protons); 6.8 (4H, s, phenyl protons); 4.6 (1H, q, CHCH3); 4.2 (2H, q, OCH2CH3); 1.6 (3H, d, CHCH3); 1.2 (3H, t, OCH2CH3).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between methylene chloride and water
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-52bbb3d1cb644ca58d873d81e3424f3b
Source dataset
uspto-grants-1984_04
Patent number
US04444584

Reaction notes

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