Methanesulfonic Acid → HCID 19749307, compound

HRID 484086Notes

Reaction equation

HRID 484086 reaction equation
Cl[C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[NH2:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH2:22][CH2:23][OH:24].CS(O)(=O)=O>CO>[OH:24][CH2:23][CH2:22][C:21]1[CH:20]=[C:19]([CH:27]=[CH:26][CH:25]=1)[NH:18][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 149389872-(3-Aminophenyl)ethan-1-olHCID 15571672HCID 15571672, compound

Product 1

HCID 19749307HCID 19749307, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9-chloro-3-methoxyacridine, (975 mg, 4 mmol), 3-aminophenethyl alcohol (549 mg, 4 ml) and methanesulfonic acid (0.32 ml, 5 mmol) in methanol (30 ml) is stirred under reflux for 2 hours. The mixture is concentrated in vacuo, and the residue is dissolved in methanol (10 ml). The solution is diluted with ether (150 ml). The precipitates are collected by filtration, washed with ether to give 9-[3'-(β-hydroxyethyl)anilino]-3-methoxyacridine, as the methanesulfonate (1.15 g, 65%), mp 186°-188° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe mixture is concentrated in vacuo
  3. dissolutionthe residue is dissolved in methanol (10 ml)
  4. additionThe solution is diluted with ether (150 ml)
  5. filtrationThe precipitates are collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-f6aca1b0e7614c3d8f6ac03d12cd91b8
Source dataset
uspto-grants-1993_07
Patent number
US05229395

Reaction notes

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