Hydrochloric Acid → HCID 18399389, compound

HRID 1019374Notes

Reaction equation

HRID 1019374 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([OH:43])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=O)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([OH:43])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18399114HCID 18399114, compound

Product 1

HCID 18399389HCID 18399389, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound obtained in Example 5 (10.0 g) is dissolved in chloroform (20 ml), and thereto are added a 4M solution of hydrogen chloride in ethyl acetate (60 ml). The mixture is stirred at room temperature overnight. The resulting suspension is neutralized with 2M aqueous sodium hydroxide solution (120 ml) under ice-cooling, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is dissolved in a small amount of ethyl acetate, and crystallized from diethyl ether to give 2-(4-aminophenyl)-7-hydroxy-6-methoxy-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (5.47 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. customThe ethyl acetate layer is separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in a small amount of ethyl acetate
  8. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-445dee5100e74a95990249c1dd2b939c
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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