Acetyl chloride → HCID 18445847, compound

HRID 460354Notes

Reaction equation

HRID 460354 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15].[C:16](Cl)(=[O:18])[CH3:17].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:12][O:11][C:10]1[C:2]([NH:1][C:16](=[O:18])[CH3:17])=[C:3]2[C:7](=[CH:8][C:9]=1[O:13][CH3:14])[C:6](=[O:15])[CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 18445650HCID 18445650, compound2×

Product 1

HCID 18445847HCID 18445847, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-5,6-dimethoxy-indan-1-one (Intermediate U) (0.214 g, 1.0 mmol) was taken up into 5 mL of DMF and acetyl chloride (0.071 mL, 1.0 mmol) and DIEA (0.18 mL, 1.0 mmol) were added. The reaction stirred overnight at room temperature. The reaction was quenched with sat. sodium bicarbonate and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and removed in vacuo. 0.25 g of the crude material was produced (Intermediate V); MS m/z 250.1 (M+H)+.

Workup

  1. additionwere added
  2. customThe reaction was quenched with sat. sodium bicarbonate
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-9ee82a4f8be6472e8ccc673997090bbf
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Reaction notes

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