Hydrochloric Acid → HCID 13236420, compound

HRID 1981299Notes

Reaction equation

HRID 1981299 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=[O:4].C1N2CN3CN(C2)C[N:17]1C3.C(O)C.Cl>CN(C)C=O>[ClH:1].[NH2:17][CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4101HexamethylenetetramineHCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 13236420HCID 13236420, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In to a suspension of 3.0 g of 6-chloroacetyl-3,4-dihydrocarbostyril being suspended in 20 ml of dimethylformamide was added dropwise gradually a solution consisting of 1.9 g of hexamine and 20 ml of dimethylformamide. After the addition was completed the reaction mixture was stirred at 50° to 60° C. for 2 hours. Then the crystals precipitated in the reaction mixture were collected by filtration, and were washed with methanol, dried to obtain 3.5 g of crude crystals of 6-hexaminiumacetyl-3,4-dihydrocarbostyril chloride. Then, 15 ml of ethanol and 6 ml of concentrated hydrochloric acid were added to the 3.5 g of the crude crystals of 6-hexaminiumacetyl-3,4-dihydrocarbostyril chloride and the mixture was stirred at a room temperature for 12 hours. The crystals thus formed were collected by filtration, and recrystallized from methanol-water to obtain 1.2 g of 6-aminoacetyl-3,4-dihydrocarbostyril monohydrochloride in the form of colorless powdery crystals. Melting point: Higher than 300° C.

Workup

  1. additionwas added dropwise gradually a solution
  2. additionAfter the addition
  3. customThen the crystals precipitated in the reaction mixture
  4. filtrationwere collected by filtration
  5. washwere washed with methanol
  6. customdried
  7. customto obtain 3.5 g of crude crystals of 6-hexaminiumacetyl-3,4-dihydrocarbostyril chloride
  8. stirringthe mixture was stirred at a room temperature for 12 hours
  9. customThe crystals thus formed
  10. filtrationwere collected by filtration
  11. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-0bae46cf2d494d988db912671f997dc1
Source dataset
uspto-grants-1985_04
Patent number
US04514401

Reaction notes

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