Chloroacetyl chloride → HCID 19067936, compound

HRID 1957545Notes

Reaction equation

HRID 1957545 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH2:19][CH:20]=[CH2:21])[C:11]([OH:18])=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:22].C(N(CC)CC)C.[Cl:30][CH2:31][C:32](Cl)=[O:33]>C(Cl)(Cl)Cl>[Cl:30][CH2:31][C:32]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH2:19][CH:20]=[CH2:21])[C:11]([OH:18])=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:22])=[O:33]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 19067902HCID 19067902, compound

Product 1

HCID 19067936HCID 19067936, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.68 Grams of 1-(3-aminopropyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone was suspended in 100 ml of chloroform, then 5 ml of triethylamine was added thereto and stirred for 30 minutes. Under ice-cooling condition, 2 ml of chloroacetyl chloride was added little by little and stirred for 5 hours. The reaction mixture was washed with water, an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate, then concentrated under reduced pressure, there was obtained 1 g (53%) of 1-(3-chloroacetylaminopropyl)-5,7-diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone. White powdery crystals (recrystallized from ethyl acetate-n-hexane). Melting point: 152°-154° C.

Workup

  1. additionwas added little by little and
  2. stirringstirred for 5 hours
  3. washThe reaction mixture was washed with water
  4. dry with materialan aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2dc6e8a032b9470bb4510bd285767717
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

Loading…