Acetyl chloride → HCID 59425609, compound

HRID 1009610Notes

Reaction equation

HRID 1009610 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)[CH3:2].[C:25](Cl)(=[O:27])[CH3:26].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[C:25]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[O:12][CH3:13])[N:3]([CH2:1][CH3:2])[C:4]([C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)=[C:5]2[C:14]#[N:15])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59425179HCID 59425179, compound

Product 1

HCID 59425609HCID 59425609, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Ethyl-6-methoxy-2-(4-nitrophenyl)-1H-indole-3-carbonitrile (100 mg, 0.3 mmol), prepared by the method of example 1Gc is suspended in 1,2-dichloroethane (500 μL) at 0° C. Acetyl chloride (50 μL, 0.69 mmol) is added, followed by AlCl3 (55 mg, 0.4 mmol) in one portion. This is stirred at 0° C. for 1 hour, at room temperature for 4 hours, and at 45° C. overnight. The reaction mixture is then partitioned between CH2Cl2 and H2O. The organic layer is dried and concentrated. Purification by silica gel chromatography (195:5 CH2Cl2/EtOAc) yields 5-acetyl-1-ethyl-6-methoxy-2-(4-nitro-phenyl)-1H-indole-3-carbonitrile (33 mg, 29%) as an orange solid.

Workup

  1. customat 45° C.
  2. customovernight
  3. customThe reaction mixture is then partitioned between CH2Cl2 and H2O
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (195:5 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-0e205976ce5649df8a55a230a71283f3
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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