Water → HCID 14171577, compound

HRID 1639252Notes

Reaction equation

HRID 1639252 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH:12]=[CH:13][CH:14]=3)[NH:9][C:10]=2[CH:11]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH3:25].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:23][CH2:24][CH3:25])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 14171570HCID 14171570, compound

Product 1

HCID 14171577HCID 14171577, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Chloropyrrolo[1,2-b]cinnolin-10(5H)-one (9.0 g) was taken up in 100 ml of DMF and milled K2CO3 (11.33 g) was added. 1-Bromopropane (10.09 g) was then added dropwise and the solution was stirred at room temperature for 48 h. Water was added and the solution was extracted into dichloromethane and washed several times with H2O and dilute hydrochloric acid. The organics were then dried (MgSO4), charcoaled, filtered and concentrated to an orange oil. The oil was purified by HPLC (silica, dichloromethane) and concentrated to give 6.33 g of an orange powder which was recrystallized from ether to yield 3.4 g of yellow-orange microcrystals, mp 107°-108°.

Workup

  1. additionwas added
  2. extractionthe solution was extracted into dichloromethane
  3. washwashed several times with H2O and dilute hydrochloric acid
  4. dry with materialThe organics were then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an orange oil
  7. customThe oil was purified by HPLC (silica, dichloromethane)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-54641d7759ed40e6a25588ddf29b6648
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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