Hydrochloric Acid → 6-Methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride

HRID 1181943Notes

Reaction equation

HRID 1181943 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][C:9]=2[N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)=[O:5])C.CO.[ClH:28]>>[ClH:28].[CH3:18][O:17][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH:10]=1)[O:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15][C:14]2=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22142223Ethyl-6-methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylate

Product 1

HCID 692667556-Methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride

Procedure

Ethyl-6-methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylate (1.0 g. 2.89 mmol), as prepared in Reference Example 2d above, was suspended in 6 M HCl (60 ml) and methanol (10 mL) and warmed to reflux for 3.0 h. The reaction was allowed to cool. The solution was concentrated in vacuo and anhydrous toluene was added (×3) and the solution was again concentrated in vacuo. The residue was dried under vacuum (17 h) to yield 6-methoxy-8-(4-methyl-1-piperazinyl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride as a yellow powder (1.0 g, quantitative yield).

Workup

  1. temperatureto reflux for 3.0 h
  2. temperatureto cool
  3. concentrationThe solution was concentrated in vacuo and anhydrous toluene
  4. additionwas added (×3)
  5. concentrationthe solution was again concentrated in vacuo
  6. customThe residue was dried under vacuum (17 h)

Sources & evidence

ORD record
ord-4ad7bd51014242d484fbe822da0cd6d4
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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