Acetyl chloride → HCID 10375665, compound

HRID 2268180Notes

Reaction equation

HRID 2268180 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C[O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[C:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:7]=1[OH:6])[NH:14][C:13](=[O:17])[CH2:12][CH2:11]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 10375665HCID 10375665, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (2.0 mL, 28.1 mmol) was added to a mixture of 3,4-dihydro-7-methoxy-2H-quinolin-2-one (1.99 g, 11.2 mmol) in 1,2-dichloroethane (30 mL). The mixture obtained was cooled to 0° C. and AlCl3 (6.0 g, 44.98 mmol) was added in portions. The mixture was heated to reflux for 2 hours. The reaction was cautiously poured over ice-H2O, stirred for a minimum of 1 hour (to overnight), and extracted with CH2Cl2. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound (1.89 g, 82%) as an off-white solid.

Workup

  1. customThe mixture obtained
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 hours
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6ae19ab2a1334733b7db04c6b0805b02
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

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