Hydrochloric Acid → HCID 18398797, compound

HRID 1019385Notes

Reaction equation

HRID 1019385 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][N:5]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:31].Cl.[C:33](OCC)(=[O:35])[CH3:34]>>[C:33]([O:1][CH2:2][CH2:3][NH:4][N:5]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([C:19]2[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:31])(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 18399015HCID 18399015, compound

Product 1

HCID 18398797HCID 18398797, compound

Procedure

To a solution of the compound obtained in Example 74 (210 mg) in ethyl acetate (10 ml) is added a 4M solution of hydrogen chloride in ethyl acetate (10 ml), and the mixture is stirred at room temperature for five hours. The reaction mixture is concentrated under reduced pressure, and the residue is dissolved in ethyl acetate. The solution is washed successively with a saturated aqueous sodium hydrogen carbonate solution and water, and dried. The solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1), and crystallized from diethyl ether to give 2-(2-acetoxyethylamino)-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone as listed in Table 6.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washThe solution is washed successively with a saturated aqueous sodium hydrogen carbonate solution and water
  4. customdried
  5. concentrationThe solution is concentrated under reduced pressure
  6. customthe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)
  7. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-b1628e7b224a420ebb0ead4ce92494de
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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