Acridine, 1,2,3,4-tetrahydro-9-chloro- → HCID 15888164, compound

HRID 1067247Notes

Reaction equation

HRID 1067247 reaction equation
Cl[C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.Cl.[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[CH2:20][O:21][NH2:22].C(=O)(O)[O-].[Na+]>C(O)CC>[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[CH2:20][O:21][NH:22][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 21495Acridine, 1,2,3,4-tetrahydro-9-chloro-HCID 516892Sodium BicarbonateHCID 21192890O-(2-Fluorobenzyl)hydroxylamine hydrochloride

Product 1

HCID 15888164HCID 15888164, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 9-chloro-1,2,3,4-tetrahydroacridine (6.18 g) and O-(2-fluorobenzyl)hydroxylamine hydrochloride (5.5 g) in 125 ml of n-propanol was heated at reflux for 20 hours. The reaction mixture was then added to an iced sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organics were washed with water and dried (saturated NaCl, MgSO4).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organics were washed with water
  5. dry with materialdried (saturated NaCl, MgSO4)

Sources & evidence

ORD record
ord-6aa04bcfbf944cffbc53482f903f7c03
Source dataset
uspto-grants-2001_06
Patent number
US06248750B1

Reaction notes

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