Formic Acid → HCID 57949729, compound

HRID 2427508Notes

Reaction equation

HRID 2427508 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]#N)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.C(O)=[O:27]>O=[Pt]=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:24]=[O:27])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2

Participants

4

Reactant 2

HCID 284Formic AcidHCID 579493637-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile

Product 1

HCID 57949729HCID 57949729, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst2×

Conditions

Temperature
60 °C

Procedure

7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (400.0 mg, 1.16 mmol) and PtO2 (26.0 mg, 0.115 mmol) were added to formic acid (2 mL) and the mixture was heated at 60° C. for three hours. The NMR spectrum showed 40% conversion, so PtO2 (50.0 mg) was added to the mixture and it was allowed to stir at 60° C. overnight. After cooling, the mixture was filtered through Celite® and concentrated. Column chromatography (30% EtOAc/Hexanes) provided the title compound as a white solid (357.5 mg, 88%). 1H NMR (300 MHz, CDCl3): δ 10.08 (s, 1H), 7.71 (s, 2H), 7.35 (d, 3H), 7.19 (d, 3H), 4.80 (s, 2H), 4.32 (s, 2H), 2.83 (s, 3H).

Workup

  1. additionwas added to the mixture and it
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a5b0d9e0f8c740b3a2d2cd210b8f9a5d
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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