Acetyl chloride → HCID 11816968, compound

HRID 1879571Notes

Reaction equation

HRID 1879571 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[OH:14].[C:15](Cl)(=[O:17])[CH3:16]>CN(C=O)C.C(Cl)Cl>[C:15]([O:14][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH:1]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 935512-Hydroxycarbazole

Product 1

HCID 11816968HCID 11816968, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 9H-carbazol-2-ol (915 mg, 5 mmol) in 10 mL DMF and 20 mL DCM was added TEA (1.0 g, 10 mmol), followed by acetyl chloride (589 mg, 7.5 mmol) at 0° C. The reaction mixture was then stirred at rt for 1 h and poured onto ice (50 g). The mixture was extracted with EtOAc (2×60 mL) and combined organic phase was dried over MgSO4 and concentrated. The crude product was purified by silica chromatography to afford 9H-carbazol-2-yl acetate (WZ02013) as an off-white solid (800 mg, 71%). MS (ESI) m/z 348 (M+H+).

Workup

  1. additionpoured onto ice (50 g)
  2. extractionThe mixture was extracted with EtOAc (2×60 mL)
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-b7c18e3daadc4dcf864221709b4326d9
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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