Hydrochloric Acid → HCID 53311336, compound

HRID 2427509Notes

Reaction equation

HRID 2427509 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.[OH-:26].[Na+].Cl.C[OH:30]>>[CH3:1][C:2]1[CH:3]=[C:4]([C:24]([OH:30])=[O:26])[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

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 579493637-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile

Product 1

HCID 53311336HCID 53311336, compoundYield 64%

Procedure

7-Methyl-1-oxo-2-(4-trifluoromethoxybenzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (103 mg, 0.30 mmol) was stirred at 100° C. in MeOH (10 mL) and 6N NaOH (10 mL) for 2.5 hours. The reaction was acidified with 1N HCl and partitioned between CH2Cl2 and water, and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to yield a white solid (69.0 mg, 64%). 1H NMR (300 MHz, CDCl3): δ 7.96 (d, 2H), 7.37 (d, 2H), 7.21 (d, 2H), 4.82 (s, 2H), 4.32 (s, 2H), 2.84 (s, 3H).

Workup

  1. custompartitioned between CH2Cl2 and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2bd637ddf1ee46e8a26327f714b1e57b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…