Chloroacetyl chloride → HCID 66936864, compound

HRID 1943712Notes

Reaction equation

HRID 1943712 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[OH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[CH2:14][C:15](Cl)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:1]1[C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]=2[O:12][CH2:14][C:15]1=[O:16]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 178507989HCID 178507989, compound

Product 1

HCID 66936864HCID 66936864, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 50 ml flask equipped with a reflux apparatus, 3-amino-quinolin-4-ol (421 mg, 2.628 mmol) was dissolved in N,N-dimethyl formamide (13 ml) under nitrogen atmosphere, and then chloroacetyl chloride (0.21 ml, 2.76 mmol) was added thereto dropwise at 0□, and then stirred at 0□ for 30 minutes. Potassium carbonate (24 g, 177 mmol) was added thereto and the mixture was heated to 100□ under reflux. After 16 hours, N,N-dimethyl formamide solvent was evaporated under reduced pressure and methanol was added to the residue, and then the mixture was filtered on celite. The filtrate was evaporated under reduced pressure to obtain the target compound, i.e., 1H-4-oxa-1,9-diaza-phenanthren-2-one, as brown solid (526 mg, quantitative yield).

Workup

  1. temperaturethe mixture was heated to 100□
  2. temperatureunder reflux
  3. waitAfter 16 hours
  4. customN,N-dimethyl formamide solvent was evaporated under reduced pressure and methanol
  5. additionwas added to the residue
  6. filtrationthe mixture was filtered on celite
  7. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ba8d1661c40f4985bd704adead8cca73
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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