N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylate → 2-(N,N-dimethylamino)ethoxybenz[b]acridine-12-carboxylic acid

HRID 1417924Notes

Reaction equation

HRID 1417924 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[C:20]2[C:19]([C:21]([O:23]CCN(C)C)=[O:22])=[C:18]3[C:13]([CH:14]=[C:15]4[CH:32]=[CH:31][CH:30]=[CH:29][C:16]4=[CH:17]3)=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:3]>[OH-].[Na+].CO>[CH3:3][N:2]([CH2:4][CH2:5][O:6][C:7]1[C:20]2[C:19]([C:21]([OH:23])=[O:22])=[C:18]3[C:13]([CH:14]=[C:15]4[CH:32]=[CH:31][CH:30]=[CH:29][C:16]4=[CH:17]3)=[N:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:1]

Participants

4

Reactant 1

HCID 86748523N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylate

Product 1

HCID 867485252-(N,N-dimethylamino)ethoxybenz[b]acridine-12-carboxylic acidYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N,N-dimethylaminoethyl 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylate (86 mg, 0.20 mmol ) in 4N sodium hydroxide (7.3 ml) and methanol (22 ml) was stirred at 65° C. for 1 hour and at 35° C. for 15 hours. The reaction mixture was evaporated under reduced pressure to dryness. The residue was washed with water (5 ml) and air-dried, yielding 2-(N,N-dimethylamino)ethoxy-benz[b]acridine-12-carboxylic acid (23 mg, 32%). Rf 0.3 (silica gel, chloroform/methanol/water 65:25:4). MS (FAB, Glycerol Matrix): m/z 361 (M+1).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure to dryness
  2. washThe residue was washed with water (5 ml)
  3. customair-dried

Sources & evidence

ORD record
ord-5b57b34ea3244a61babe02fdf7f131b4
Source dataset
uspto-grants-1999_03
Patent number
US05879894

Reaction notes

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