Hydrochloric Acid → HCID 18398822, compound

HRID 1019399Notes

Reaction equation

HRID 1019399 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:38]3[CH:43]=[C:42]([O:44][CH3:45])[C:41]([Br:46])=[C:40]([O:47][CH3:48])[CH:39]=3)=[C:14]([C:34]([O:36][CH3:37])=[O:35])[N:15]([C:20]3[CH:25]=[CH:24][C:23]([NH:26]C(OC(C)(C)C)=O)=[CH:22][CH:21]=3)[C:16]2=[O:19])=[CH:11][C:10]=1[O:49][CH3:50])C1C=CC=CC=1.Cl.[OH-].[Na+].C(=O)([O-])O.[Na+]>O1CCOCC1.CO>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([N:15]2[C:14]([C:34]([O:36][CH3:37])=[O:35])=[C:13]([C:38]3[CH:43]=[C:42]([O:44][CH3:45])[C:41]([Br:46])=[C:40]([O:47][CH3:48])[CH:39]=3)[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:49][CH3:50])[CH:11]=3)[C:16]2=[O:19])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 18399334HCID 18399334, compound

Product 1

HCID 18398822HCID 18398822, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

The compound obtained in Example 317 (3.66 g) is dissolved in 1,4-dioxane (45 ml), and thereto are added conc. hydrochloric acid (50 ml) and methanol (5 ml). The mixture is heated with stirring at 90° C. for 1.5 hour. To the mixture is added gradually a 2M aqueous sodium hydroxide solution (200 ml) under ice-cooling, and the mixture is neutralized with a saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted with ethyl acetate, and the extract is washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 2-(4-aminophenyl)-4-(4-bromo-3,5-dimethoxyphenyl)-7-hydroxy-6-methoxy-3-methoxycarbonyl-1(2H)-isoquinolinone (2.54 g) as listed in Table 27.

Workup

  1. temperatureThe mixture is heated
  2. temperaturecooling
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe extract is washed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-a10a1469b050471c83c5b596af01238b
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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