Acetyl chloride → HCID 13160404, compound

HRID 2305591Notes

Reaction equation

HRID 2305591 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, compound

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 (0.1 8 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, 1H); 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) 12.6 (s, 3H), 4.35 (q, 2H), 7.3 (s, 1H), 7.5 (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-4a69237a9b0a47bdbcfbd4c046306d5e
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

Loading…