4-Toluenesulfonyl chloride → HCID 24852050, compound

HRID 415517Notes

Reaction equation

HRID 415517 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][C:13]3=[N:12][C:4]=1[CH:5]=[N+:6]2[O-].[NH4+:18].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][C:13]3=[N:12][C:4]=1[C:5]([NH2:18])=[N:6]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66619921HCID 66619921, compound

Product 1

HCID 24852050HCID 24852050, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8,9-dihydroisoxazolo[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (0.0499 g, 0.220 mmol) in dichloromethane from the previous step was treated with 1.5 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (0.046 g, 0.242 mmol) was carefully added. Rapid stirring was continued for 5 minutes. The reaction mixture was then diluted with more dichloromethane, washed successively with dilute aqueous K2CO3, H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography (SiO2, 0-15% CMA/CHCl3) gave 0.015 g of 8,9-dihydroisoxazolo[2′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a brown solid, mp greater than 300° C.

Workup

  1. stirringRapid stirring
  2. washwashed successively with dilute aqueous K2CO3, H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76f8d2b666d14d0ea41cc629be8467e5
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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