Acetyl chloride → HCID 13160404, compound

HRID 967109Notes

Reaction equation

HRID 967109 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]>ClCCCl>[C:1]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[NH:9][C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 73125Ethyl indole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13160404HCID 13160404, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Acetyl chloride (0.76 ml) was added to a suspension of anhydrous aluminium (III) chloride (1.42 g) in 1,2-dichloroethane (20 ml) at 0° C. The reaction was stirred for 5 minutes then a solution of ethyl indole-2-carboxylate (1 g) in 1,2-dichloroethane (20 ml) was added dropwise over 10 minutes. The reaction was heated at reflux for 1 hour, cooled and poured into ice/water. The solution was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-10% ethyl acetate as eluent to give firstly ethyl 7-acetylindole-2-carboxylate as a white solid (0.18 g, 15%); NMR δ (CD3SOCD3) 1.35 (t, 3H), 2.7 (s, 3H), 4.4 (q, 2H), 7.3 (m, 2H), 8.05 (m, 2H), 10.7 (bs, 11H); M/z (+) 232 (MH+), followed by ethyl 3-acetylindole-2-carboxylate as a white solid (0.2 g, 16%); NMR δ (CD3SOCD3) 1.35 (t, 3H), 2.6 (s, 3H), 4.4 (q, 2H), 7.2 (t, 1H), 7.3 (t, 1H), 7.5 (d, 1H), 7.9 (d, 1H), 12.4 (bs, 1H); M/z (+) 232 (MH+), followed by ethyl 5-acetylindole-2-carboxylate as a white solid (0.5 g, 42%); NMR δ (CD3SOCD3) 1.35 (t, 3H), 2.6 (s, 3H), 4.35 (q, 2H), 7.3 (s, 1H), 7.5 (d, 1H), 7.85 (d, 1H), 8.4 (s, 1H), 12.2 (bs, 1H); M/z (+) 232 (MH+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. customThe solution was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialCombined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-0555b9378a1a4af1ba22bc8a4bdfaee9
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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