Pyridine → HCID 18399207, compound

HRID 1019381Notes

Reaction equation

HRID 1019381 reaction equation
[NH2:1][N:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:28].N1C=CC=CC=1.[C:35](Cl)(=[O:37])[CH3:36].C(OCC)(=O)C>O1CCCC1.O>[C:35]([NH:1][N:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:28])(=[O:37])[CH3:36]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 18399304HCID 18399304, compound

Product 1

HCID 18399207HCID 18399207, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the compound obtained in Example 68 (200 mg) and pyridine (120 mg) in tetrahydrofuran (15 ml) is added dropwise a solution of acetyl chloride (61.3 mg) in tetrahydrofuran (5 ml) under ice-cooling, and the mixture is stirred under ice-cooling for one hour, and further stirred at room temperature overnight. To the reaction mixture are added ethyl acetate and water, and the ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from a mixture of hexanediethyl ether to give 2-acetylamino-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (116 mg) as listed in Table 6.

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour
  3. stirringfurther stirred at room temperature overnight
  4. customthe ethyl acetate layer is separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is crystallized from a mixture of hexanediethyl ether

Sources & evidence

ORD record
ord-43b5bc00714247efa08ee81d09f6e2f5
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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