Acetic Anhydride → Ethyl 5-acetoxyindole-2-carboxylate

HRID 1166056Notes

Reaction equation

HRID 1166056 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C1C=CN=CC=1)C>[C:16]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 11379620Ethyl 5-acetoxyindole-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A stirred solution of ethyl 5-hydroxyindole-2-carboxylate (7.79 g) and DMAP (20 mg) in acetic anhydride (80 ml) was heated at 80° C. for 4 hours. The reaction was concentrated in vacuo and the residue was dissolved in ethyl acetate. Combined organic extracts were washed with hydrochloric acid (2.0 M), saturated aqueous sodium hydrogen carbonate solution, water, aqueous saturated sodium chloride solution and dried (MgSO4). The solution was concentrated in vacuo to give the product as a yellow solid (9.39 g, 100%): NMR δ(CD3SOCD3) 1.20 (t, 3H), 2.10 (s, 3H), 4.19 (q, 2H), 6.86 (dd, 1H), 6.97 (d, 1H), 7.20 (s, 1), 7.29 (d, 1H); M/z (+) 248 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washCombined organic extracts were washed with hydrochloric acid (2.0 M), saturated aqueous sodium hydrogen carbonate solution, water, aqueous saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-b64fa016d23e4dd3a736454e68bc8c64
Source dataset
uspto-grants-2003_09
Patent number
US06613760B1

Reaction notes

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