Water → N-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 2173344Notes

Reaction equation

HRID 2173344 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:13])[CH3:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH2:14]>C(O)(=O)C.C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[O:14]=[C:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:13])[CH3:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 962WaterHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 312894N-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetamide

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of N-(2,3-dihydro-1H-inden-5-yl)acetamide (50 g, 0.29 mol) in 150 mL of acetic acid and 40 mL of actic anhydride was added a solution of chromium trioxide in a mixed solution (30 mL of water and 140 mL of acetic acid) dropwise at 10° C. by external cooling. After stirring overnight, the solution was poured into 2 L of ice water under vigorously stirring. The resulting solid was filtered, washed with cooled EtOH to give N-(1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide. 1H-NMR (300 MHz, CDCl3) δ ppm 7.90 (s, 1H), 7.66˜7.70 (m, 2H), 7.22˜7.25 (m, 1H), 3.09˜3.13 (m, 2H), 2.66˜2.70 (m, 2H), 2.22 (s, 3H);

Workup

  1. stirringunder vigorously stirring
  2. filtrationThe resulting solid was filtered
  3. washwashed with cooled EtOH

Sources & evidence

ORD record
ord-cd08d57dafea442cbb20056f6e992f67
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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