Acetic Acid → HCID 135705340, compound

HRID 1283172Notes

Reaction equation

HRID 1283172 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH2:14])=[O:13])=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:21](OCC)(=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(O)(=O)C>CCOCC>[C:15]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]3[N:1]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:14][C:12](=[O:13])[C:11]=23)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 218217142-Amino-4-phenyl-3-quinolinecarboxamide

Product 1

HCID 135705340HCID 135705340, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-amino-4-phenylquinoline-3-carboxamide (263 mg., 1.0 millimole), diethyl oxalate (5 ml.) acetic acid (5 ml.) is heated to reflux overnight. It is then cooled, diluted with ether (50 ml.) and the brown solid which forms filtered off. The filtrate is evaporated in vacuo and the oily residue triturated with saturated aqueous sodium bicarbonate solution. The resulting solid (110 mg.) is recovered by filtration and recrystallized from hot ethyl acetate (8 ml.). A small amount of insoluble material is filtered off from the hot solution. Upon cooling, the title product separates as crystals (25 mg.). M.P. = 255° C. (dec.).

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. temperatureIt is then cooled
  4. filtrationthe brown solid which forms filtered off
  5. customThe filtrate is evaporated in vacuo
  6. customthe oily residue triturated with saturated aqueous sodium bicarbonate solution
  7. filtrationThe resulting solid (110 mg.) is recovered by filtration
  8. customrecrystallized from hot ethyl acetate (8 ml.)
  9. filtrationA small amount of insoluble material is filtered off from the hot solution
  10. temperatureUpon cooling

Sources & evidence

ORD record
ord-13cdbceeb8e54b0493e41c8a4ae02a8d
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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