8-Aminoquinoline → HCID 178512524, compound

HRID 1709315Notes

Reaction equation

HRID 1709315 reaction equation
Cl.[NH:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[C:3]([NH2:5])=[NH:4].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.S(Cl)(Cl)=O.[NH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[CH:39][CH:38]=[CH:37]2>O.O1CCCC1>[NH:2]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:31][C:32]2[CH:33]=[CH:34][CH:35]=[C:36]3[C:41]=2[N:40]=[CH:39][CH:38]=[CH:37]3)=[O:12])=[CH:13][CH:14]=1)[C:3]([NH2:5])=[NH:4]

Participants

7

Reactant 4

HCID 113598-AminoquinolineHCID 24386Thionyl ChlorideHCID 11708267BistrimethylsilylacetamidHCID 178479383HCID 178479383, compound

Product 1

HCID 178512524HCID 178512524, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 200 mg. (0.92 m. mol) 4-guanidinobenzoic acid hydrochloride and 190 mg. (0.93 m. mol) of bis-trimethylsilylacetamide in 20 ml. of dry tetrahydrofuran was heated at reflux until a solution was achieved, and then cooled to room temperature. Thionyl chloride (380 mg., 1.86 m. mol) was added and the reaction mixture allowed to stir for 5 min. 8-Aminoquinoline (670 mg., 4.64 m. mol) was added in 5 ml. of tetrahydrofuran and the mixture allowed to stir for 30 min. Water (0.2 ml) was added to the reaction mixture and the solids filtered and dissolved in 60 ml. of methanol and 120 ml. of chloroform. Addition of diethyl ether precipitated the desired product, 153 mg., m.p. 271°-273° C.

Workup

  1. additionA mixture of 200 mg
  2. temperatureat reflux until a solution
  3. stirringto stir for 30 min
  4. filtrationthe solids filtered
  5. dissolutiondissolved in 60 ml
  6. additionAddition of diethyl ether
  7. customprecipitated the desired product, 153 mg

Sources & evidence

ORD record
ord-8379c61a71074ac6b35ef05b55f64437
Source dataset
uspto-grants-1990_08
Patent number
US04948901

Reaction notes

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