Benzenepropanoyl chloride → HCID 178418272, compound

HRID 1451301Notes

Reaction equation

HRID 1451301 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([OH:18])=[C:7]3[C:15](=[O:16])[NH:14][NH:13][C:12](=[O:17])[C:8]3=[N:9][C:10]=2[CH:11]=1.[C:19](Cl)(=[O:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([OH:18])=[C:7]3[C:15]([O:16][C:19](=[O:28])[CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:14][NH:13][C:12](=[O:17])[C:8]3=[N:9][C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 178418421HCID 178418421, compound

Product 1

HCID 178418272HCID 178418272, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 7-chloro-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (0.60 g, 2.3 mM), as prepared in Example 2, and hydrocinnamoyl chloride (1.15 g, 6.84 mM) in pyridine (9 mL) was refluxed for 1 hr. Upon cooling to room temperature, the solution solidified. After 2 hr at room temperature, the mixture was diluted with water (60 mL) and the solids broken up with a glass rod to provide a free-flowing aqueous suspension which was stirred for 1 hr. The solids were collected, washed with water (10 mL), and resuspended in 50% aqueous methanol (60 mL). After stirring for 15 minutes, this suspension was filtered and the collected solids were washed with 50% aqueous methanol (10 mL) and then sucked dry under a stream of nitrogen to provide a tan solid. This material was dried for 2.5 days in vacuo (50 mTorr) at 100° C. and then was recrystallized from dimethylsulfoxide/methanol. The title compound was obtained (0.40 g, 44%), after drying 24 hr in vacuo (50 mTorr) at 100° C., as an off-white powder, mp >300° C. Analysis for C20H14ClN3O4 ·0.3 H2O: Calculated: C, 60.0; H, 3.65; N, 10.50 Found: C, 60.1; H, 3.69; N, 10.56

Workup

  1. temperaturewas refluxed for 1 hr
  2. customto provide a free-flowing aqueous suspension which
  3. customThe solids were collected
  4. washwashed with water (10 mL)
  5. stirringAfter stirring for 15 minutes
  6. filtrationthis suspension was filtered
  7. washthe collected solids were washed with 50% aqueous methanol (10 mL)
  8. customsucked dry under a stream of nitrogen
  9. customto provide a tan solid
  10. customThis material was dried for 2.5 days in vacuo (50 mTorr) at 100° C.
  11. customwas recrystallized from dimethylsulfoxide/methanol

Sources & evidence

ORD record
ord-50944d9a4c15493789ee932968230af9
Source dataset
uspto-grants-1997_02
Patent number
US05604227

Reaction notes

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