Hydrochloric Acid → HCID 178466753, compound

HRID 544403Notes

Reaction equation

HRID 544403 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[OH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[C:22](Cl)=[O:23].Cl>N1C=CC=CC=1>[OH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[C:22]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH:6]=1)=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 90764-EthoxyanilineHCID 178521122HCID 178521122, compound

Product 1

HCID 178466753HCID 178466753, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.86 g of phenetidine were added to a suspension of 3 g of 4-hydroxy-3-quinoline-carboxylic acid chloride (described in French Pat. No. 2,340,735) in 40 ml of anhydrous pyridine and the mixture was stirred for 16 hours. 50 ml of aqueous 2 N hydrochloric acid solution were added to the mixture which was stirred for one hour and then was filtered. The recovered product was washed with water, dried at 180° C. under reduced pressure and was crystallized from 30 ml of acetic acid and then 10 ml of dimethylformamide to obtain 2.1 g of 4-hydroxy-N-(4-ethoxyphenyl)-3-quinoline-carboxamide in the form of crystals melting at 288° C.

Workup

  1. filtrationwas filtered
  2. washThe recovered product was washed with water
  3. customdried at 180° C. under reduced pressure
  4. customwas crystallized from 30 ml of acetic acid

Sources & evidence

ORD record
ord-7661a0d850014a958ab6874a2a660ee5
Source dataset
uspto-grants-1984_05
Patent number
US04450167

Reaction notes

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