HCID 86761171, compound → 3-bis(3,5-dimethylphenyl)phosphino-2H-isoquinolin-1-one

HRID 1712220Notes

Reaction equation

HRID 1712220 reaction equation
C([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([P:16]([C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=2)[C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=2)[N:7]=1)(C)(C)C>C(O)=O>[CH3:23][C:21]1[CH:22]=[C:17]([P:16]([C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=2)[C:8]2[NH:7][C:6](=[O:5])[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:18]=[C:19]([CH3:24])[CH:20]=1

Participants

3

Reactant 1

HCID 86761171HCID 86761171, compound

Product 1

HCID 509016373-bis(3,5-dimethylphenyl)phosphino-2H-isoquinolin-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-tert-butoxy-3-(bis(3,5-dimethylphenyl)phosphino)isoquinoline (0.96, 2.2 mmol) is dissolved in neat concentrated formic acid (9 mL), and the solution is stirred at ambient temperature for 1 hour. Precipitation of the isoquinolone was induced by dilution with H2O (25 mL), and the suspension is filtered through a glass frit. The white flakes are washed with 70% formic acid solution (3×5 mL). The combined aqueous formic acid filtrates are concentrated under reduced pressure, and the opaque residue is crystallized from acetone yielding 3-bis(3,5-dimethylphenyl)phosphino-2H-isoquinolin-1-one (0.55 g, 66%).

Workup

  1. customPrecipitation of the isoquinolone
  2. filtrationthe suspension is filtered through a glass frit
  3. washThe white flakes are washed with 70% formic acid solution (3×5 mL)
  4. concentrationThe combined aqueous formic acid filtrates are concentrated under reduced pressure
  5. customthe opaque residue is crystallized from acetone

Sources & evidence

ORD record
ord-26304ce7f9a347d68ee26446158c69bb
Source dataset
uspto-grants-2010_09
Patent number
US07790932B1

Reaction notes

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