Formamidine acetate → HCID 135624001, compound

HRID 613545Notes

Reaction equation

HRID 613545 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:23]([O:25]CC)=O.C(O)(=O)C.[CH:32]([NH2:34])=[NH:33]>CN1CCCC1=O>[Cl:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:21])[C:14]=1[C:13]([NH:12][C:7]1[C:6]2[N:5]=[CH:4][C:3]3[C:23](=[O:25])[NH:34][CH:32]=[N:33][C:2]=3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:22]

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 19592702HCID 19592702, compound

Product 1

HCID 135624001HCID 135624001, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (200 mg), formamidine acetate (246 mg) and N-methylpyrrolidone was stirred for 4 hours at 100° C., for 45 minutes at 120° C. and for 6 hours at 130° C. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and evaporated in vacuo. The residue was crystallized from isopropyl alcohol and collected by filtration to give 7-(2,6-dichlorobenzoylamino)-3,4-dihydropyrimido[5,4-c]quinolin-4-one (116 mg).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with water
  3. customevaporated in vacuo
  4. customThe residue was crystallized from isopropyl alcohol
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a9ff1dbfe14d4e4d814f427f86e27e64
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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