Potassium Carbonate → HCID 22176044, compound

HRID 1797479Notes

Reaction equation

HRID 1797479 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH3:30])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1)=[CH:16][C:15]([Cl:28])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH3:30])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)=[CH:16][C:15]([Cl:28])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 22175819HCID 22175819, compound

Product 1

HCID 22176044HCID 22176044, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tert-butyl{6-chloro-2-methyl-1-oxo-4-(3-nitrophenyl)-1,2-dihydro-3-isoquinolinyl}methylcarbamate (synthesized according to the method similar to that in Example 23 (6)) (0.89 g, 2 mmol) was added to an aqueous solution (10 ml) of potassium carbonate (2.90 g, 21 mmol) and sodium hydrosulfite (2.44 g, 14 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. After washing the extract with water, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl{4-(3-aminophenyl)-6-chloro-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.48 g, 58.5%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing the
  3. extractionextract with water
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1dd2f93013e84977a5a351b44d21f1a0
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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