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

HRID 1466082Notes

Reaction equation

HRID 1466082 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 acetic anhydride was added dropwise to a solution of chromium trioxide in a mixed solution (30 mL of water and 140 mL of acetic acid) at a temperature of 10° C. (achieved by external cooling). After stirring overnight, the solution was poured into 2 L of ice water with vigorous stirring. The resulting solid was filtered and washed with cooled EtOH to give the title compound.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with cooled EtOH

Sources & evidence

ORD record
ord-289c952f8d264b8bac920b52495c8ba9
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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