Potassium Carbonate → HCID 20296712, compound

HRID 1389512Notes

Reaction equation

HRID 1389512 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH:7]2[CH2:12][C:13](=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[H][H]>C(O)C.[Pd]>[CH3:17][O:16][C:5]1[CH:4]=[CH:3][CH:2]=[C:10]2[C:6]=1[CH:7]([CH2:12][C:13](=[O:15])[CH3:14])[NH:8][C:9]2=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 20296661HCID 20296661, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20296712HCID 20296712, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-bromo-1,3-dihydro-4-methoxy-3-(2-oxopropyl)-2H-isoindol-1-one (5.0 g, described in Example 20) and potassium carbonate (2.5 g) in ethanol (100 ml) is hydrogenated in the presence of 5% palladium on carbon (2.5 g) at atmospheric pressure and room temperature until 1.1 equivalent of hydrogen is absorbed. The mixture is filtered and the filtrate is evaporated. A solution of the residue in chloroform is washed with water, dried and evaporated. The residue is crystallized from dichloromethane-diethyl ether to give the title compound (2.7g): mp 176.5°-177.5° C.; nmr (CDCl3) δ 2.20 (s, 3H), 2.30 (2d, 2H), 3.57 (2d, 2H), 3.87 (s, 3H), 4.85 (2d, 1H), 6.70(s, 1H), 6.97 (t, 1H) and 7.37(d, 2H); and Anal. Calcd for C12H13NO3 : C, 65.74 % H, 5.98% N, 6.39% and Found: C, 65.64% H, 6.09% N, 6.70%.

Workup

  1. customis absorbed
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. washA solution of the residue in chloroform is washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-239ca1c801534f26aca12991d386012f
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Reaction notes

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