Acetic Anhydride → Methyl 4-acetoxyindole-2-carboxylate

HRID 967111Notes

Reaction equation

HRID 967111 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.[C:15](OC(=O)C)(=[O:17])[CH3:16]>CN(C)C1C=CN=CC=1>[C:15]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22310940Methyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 22310858Methyl 4-acetoxyindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
80 °C

Procedure

Methyl 4-hydroxyindole-2-carboxylate (0.5 g) and 4-dimethylaminopyridine (50 mg) were dissolved in acetic anhydride (5 ml) and heated at 80° C. for 3 hours. The reaction was allowed to cool overnight to precipitate white crystals, which were filtered and dried in vacuo (0.44 g, 72%); NMR δ (CD3SOCD3) 2.34 (s, 3H), 3.85 (s, 3H), 6.80 (d, 1H), 7.06 (s, 1H), 7.23 (t, 1H), 7.29-7.35 (m, 1H), 12.1 (bs, 1H); M/z (−) 232 (M−H+).

Workup

  1. temperatureto cool overnight
  2. customto precipitate white crystals, which
  3. filtrationwere filtered
  4. customdried in vacuo (0.44 g, 72%)

Sources & evidence

ORD record
ord-91fcb033532a4634b61fc9e69f0abe6f
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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