6-Amino-1-hexanol → 1,10-Phenanthrolin-5-amine

HRID 341911

Reaction equation

HRID 341911 reaction equation
CO[C:3]1[C:4](OC)=[CH:5][C:6]2S[C:9]([C:11]3[CH:19]=CC(C(O)=O)=CC=3)=[N:8][C:7]=2[CH:20]=1.ClC(OCC(C)C)=O.C([N:33](C(C)C)C(C)C)C.[NH2:40][CH2:41][CH2:42][CH2:43]CCCO>CN(C)C=O>[NH2:33][C:4]1[CH:3]=[C:20]2[C:7]([N:8]=[CH:9][CH:11]=[CH:19]2)=[C:6]2[C:5]=1[CH:43]=[CH:42][CH:41]=[N:40]2

Participants

6

Reactant 4

HCID 199606-Amino-1-hexanolHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 545595244-(5,6-Dimethoxybenzothiazolyl)benzoic acid

Product 1

HCID 6069701,10-Phenanthrolin-5-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of dimethylformamide was dissolved 0.26 g (0.8 mmol) of Compound (1), which is 4-(5,6-dimethoxybenzothiazolyl)benzoic acid. Further, 0.12 ml (0.9 mmol) of isobutyl chloroformate and 0.16 ml (0.9 mmol) of ethyl diisopropylamine were added thereto, followed by stirring at room temperature for 1 hour. Then, 0.10 g (0.9 mmol) of 6-aminohexanol was added thereto, followed by stirring for 1 hour and a half. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.15 g of Compound (2).

Workup

  1. stirringby stirring for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-918d6540c61f44abad59523d3c0f65bd
Source dataset
uspto-grants-1999_01
Patent number
US05856479

Linked notes

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