Acetic Anhydride → HCID 25138871, compound

HRID 1669180Notes

Reaction equation

HRID 1669180 reaction equation
[CH2:1]([N:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=2)[CH2:4]1)[CH3:2].CCN(CC)CC.[CH3:22][C:23](OC(C)=O)=[O:24]>CO.[Pd]>[CH2:1]([N:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:12][C:23](=[O:24])[CH3:22])[CH:9]=2)[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 251398882-Ethyl-2,3-dihydro-5-nitro-1H-isoindole

Product 1

HCID 25138871HCID 25138871, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of isoindole 245 (3.20 g, 16.7 mmol) in MeOH (100 mL) was stirred with Pd/C (5%, 300 mg) under H2 (60 psi) for 16 h. The solution was filtered through Celite, washed with MeOH (3×20 mL) and the solvent evaporated. The residue was dissolved in DCM (130 mL) and Et3N (13 mL, 93 mmol), Ac2O (13 mL, 138 mmol) was added dropwise and the solution stirred at 20° C. for 15 h. The mixture was partitioned between DCM and aqueous Na2CO3 solution. The organic solution was washed with water, dried and the solvent was evaporated to give acetamide 246 (3.00 g, 88%) as a dark oil: 1H NMR δ 7.45 (br s, 1H, H-4), 7.30 (br s, 1H, NH), 7.18 (br d, J=8.0 Hz, 1H, H-6), 7.12 (d, J=8.0 Hz, 1H, H-7), 3.90 (s, 2H, H-1), 3.87 (s, 2H, H-3), 2.76 (q, J=7.2 Hz, 2H, CH2), 2.15 (s, 3H, COCH3) 1.19 (t, J=7.2 Hz, 3H, CH3); HRMS (FAB+) calcd for C12H17N2O (MH+) m/z 203.1184, found 203.1188.

Workup

  1. filtrationThe solution was filtered through Celite
  2. washwashed with MeOH (3×20 mL)
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in DCM (130 mL)
  5. customThe mixture was partitioned between DCM and aqueous Na2CO3 solution
  6. washThe organic solution was washed with water
  7. customdried
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9cdc3eba8dbd4c94b4a1dc1fa47b7721
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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