6-Aminoquinoline → 6-Aminoquinolyl-N-hydroxysuccinimidyl carbamate

HRID 487721Notes

Reaction equation

HRID 487721 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:12]1[C:17](=[O:18])[N:16]([O:19][C:20](ON2C(=O)CCC2=O)=[O:21])[C:14](=[O:15])[CH2:13]1>C(#N)C>[CH2:12]1[C:17](=[O:18])[N:16]([O:19][C:20]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][CH:6]=[CH:5][C:4]=3[CH:3]=2)=[O:21])[C:14](=[O:15])[CH2:13]1

Participants

4

Reactant 2

HCID 113736-AminoquinolineHCID 676246Di(succinimido) carbonate

Product 1

HCID 27625536-Aminoquinolyl-N-hydroxysuccinimidyl carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

6-Aminoquinolyl-N-hydroxysuccinimidyl carbamate was synthesized according to the following procedure. Acetonitrile (500 ml, Baker analyzed HPLC grade) was distilled to azeotropically remove any water present. The first 50 ml of acetonitrile was discarded. 6-Aminoquinoline (1.5 g, 10 mmol, Aldrich Chemical Co.) was dissolved in 50 ml of acetonitrile and placed in an addition funnel. Di(N-succinimidyl) carbonate (DSC; 3 g., 12 mmol, Fluka Chemical Co.) was dissolved in 100 ml. of acetonitrile and heated to reflux with stirring. The aminoquinolino solution was added dropwise to the refluxing solution over a period of about 30 minutes.

Workup

  1. distillationAcetonitrile (500 ml, Baker analyzed HPLC grade) was distilled
  2. customto azeotropically remove any water present
  3. customplaced in an addition funnel
  4. temperatureto reflux
  5. additionThe aminoquinolino solution was added dropwise to the refluxing solution over a period of about 30 minutes

Sources & evidence

ORD record
ord-68b14fbdd1424b9cb7a1b106a29a42de
Source dataset
uspto-grants-1994_03
Patent number
US05296599

Reaction notes

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