HCID 53914196, compound → HCID 54189811, compound

HRID 1608488Notes

Reaction equation

HRID 1608488 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]3[C:13](=[C:14]([C:17]([O:19]C)=[O:18])[C:15]=2[CH:16]=1)[CH:12]=[C:11]1[CH:21]=[CH:22][CH:23]=[CH:24][C:10]1=[CH:9]3>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]3[C:13](=[C:14]([C:17]([OH:19])=[O:18])[C:15]=2[CH:16]=1)[CH:12]=[C:11]1[CH:21]=[CH:22][CH:23]=[CH:24][C:10]1=[CH:9]3

Participants

4

Reactant 1

HCID 53914196HCID 53914196, compound

Product 1

HCID 54189811HCID 54189811, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 2-methoxy-benz[b]acridine-12-carboxylate (35 mg, 0.10 mmol) in 4N sodium hydroxide (3 ml) and methanol (9 ml) was stirred at 65° C. for 15 hours. The resulting mixture was evaporated under reduced pressure to dryness. The residue was dissolved in water (40 ml); the aqueous solution was acidified to pH 5 with concentrated HCl in an ice-water bath. The precipitate was collected and washed with water (5 ml), yielding 2-methoxybenz[b]acridine-12-carboxylic acid (20 mg, 59%). Rf 0.5 (silica gel, chloroform/methanol/water 65:25:4). MS (CI, CH4: m/z 304 (M+1).

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to dryness
  2. dissolutionThe residue was dissolved in water (40 ml)
  3. customthe aqueous solution was acidified to pH 5 with concentrated HCl in an ice-water bath
  4. customThe precipitate was collected
  5. washwashed with water (5 ml)

Sources & evidence

ORD record
ord-8628ec5a986b4a7bae0caae429f134e0
Source dataset
uspto-grants-1995_03
Patent number
US05395752

Reaction notes

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