Methanol → HCID 18398821, compound

HRID 1019375Notes

Reaction equation

HRID 1019375 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([O:36]C)=[O:35])=[CH:30][CH:29]=2)[C:7](=[O:27])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4].CO.[OH-].[Na+].O>C(OCC)(=O)C>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([N:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:14]([C:15]3[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=3)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:27])=[CH:29][CH:30]=1)([OH:36])=[O:35]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 18399287HCID 18399287, compound

Product 1

HCID 18398821HCID 18398821, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To the compound obtained in Example 20 (1.51 g) are added methanol (150 ml) and 1M aqueous sodium hydroxide solution (3 ml), and the mixture is stirred at 60° C. overnight. To the reaction solution is further added 1M aqueous sodium hydroxide solution (1.5 ml) which is divided to two portions, and the mixture is refluxed for 12 hours. The reaction mixture is allowed to stand for cooling, and thereto are added water and ethyl acetate. The aqueous layer is separated, and acidified with hydrochloric acid, and further extracted with ethyl acetate. The ethyl acetate layers are combined, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 2-(4-carboxyphenyl)-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (245 mg) as listed in Table 4.

Workup

  1. temperaturethe mixture is refluxed for 12 hours
  2. temperaturefor cooling
  3. customThe aqueous layer is separated
  4. extractionfurther extracted with ethyl acetate
  5. washwashed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-1498ca3475354a2497f17a1a1aba3763
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

Loading…