Ammonia → 2-(4-Chlorobenzoylamino)-3-(2-quinolon-4-yl)propionamide

HRID 2225351Notes

Reaction equation

HRID 2225351 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH:9]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16](=[O:24])[CH:15]=2)[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.C([N:29](CC)CC)C.ClC(OCC(C)C)=O.N>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16](=[O:24])[CH:15]=2)[C:10]([NH2:29])=[O:12])=[O:7])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 5042RebamipideHCID 8471TriethylamineHCID 62365Isobutyl chloroformate

Product 1

HCID 134715702-(4-Chlorobenzoylamino)-3-(2-quinolon-4-yl)propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.8 Grams of 2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid was dissolved in 80 ml of N,N-dimethylformamide. To this solution was added 0.6 g of triethylamine. Then, under ice-cooled condition with stirring, 0.8 g of isobutyl chloroformate was added to the above-mentioned mixture. At the same temperature condition, 10 ml of N,N-dimethylformamide solution containing 0.4 g of ammonia was added dropwise to the reaction mixture, and stirred for 3 hours. After the removal of N,N-dimethylformamide by distillation, water was added to the residue and the crystals precipitated were collected by filtration, and were washed with an aqueous solution of sodium hydroxide. Recrystallized from dimethylformamide-water to obtain 0.7 g of 2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionamide in the form of light yellowish powdery product.

Workup

  1. temperatureThen, under ice-cooled condition
  2. additionwas added dropwise to the reaction mixture
  3. stirringstirred for 3 hours
  4. customAfter the removal of N,N-dimethylformamide
  5. distillationby distillation, water
  6. additionwas added to the residue
  7. customthe crystals precipitated
  8. filtrationwere collected by filtration
  9. washwere washed with an aqueous solution of sodium hydroxide
  10. customRecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-048cc8466a664e568c105c9631998a49
Source dataset
uspto-grants-1994_09
Patent number
USRE034722

Reaction notes

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