Hydrochloric Acid → 120067-47-2

HRID 326252Notes

Reaction equation

HRID 326252 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:15].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CN(C)C=O>[C:16]([C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[NH:5][C:6](=[O:15])[CH2:7][CH2:8]2)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 64796HydrocarbostyrilHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14373255120067-47-2Yield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred amount of 45.3 parts of aluminiumtrichloride were added dropwise 6.9 parts of N,N-dimethylformamide. After stirring for 5 min. at 70° C., there were added portionwise 5 parts of 3,4-dihydroquinolin-2(1H)-one and, after another 5 min., 4.7 parts of benzoylchloride. Stirring at 70° C. was continued for 2 hours and then the reaction mixture was carefully poured into ice-water. There were added 50 ml of HCl 12N and the whole was stirred for 15 min. The precipitate was filtered off and boiled in 2-propanol. The product was filtered off, washed with 2-propanol and 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 6.3 parts (73.8%) of 6-benzoyl-3,4-dihydro-2(1H)-quinolinone; mp. 211.0° C. (interm. 18).

Workup

  1. waitafter another 5 min.
  2. stirringStirring at 70° C.
  3. waitwas continued for 2 hours
  4. stirringthe whole was stirred for 15 min
  5. filtrationThe precipitate was filtered off
  6. filtrationThe product was filtered off
  7. washwashed with 2-propanol and 2,2'-oxybispropane
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-af427a45aacd4a259f47b39031dc5c12
Source dataset
uspto-grants-1993_12
Patent number
US05268380

Reaction notes

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