Acetic Anhydride → HCID 18522118, compound

HRID 413793Notes

Reaction equation

HRID 413793 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[NH:6]2.[C:17](OC(=O)C)(=[O:19])[CH3:18]>CN(C1C=CN=CC=1)C>[C:17]([O:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[NH:6]2)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18522144HCID 18522144, compound

Product 1

HCID 18522118HCID 18522118, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A stirred solution of methyl 4-hydroxy-5-methoxyindole-2-carboxylate (0.51 g) and DMAP (10 mg) in acetic anhydride (5 ml) was heated at 80° C. for 4 hours. The reaction was concentrated in vacuo and the residue dissolved in dichloromethane and 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 and the residue was purified by column chromatography using 50% diethyl ether:iso-hexane as eluent to give the product as a white solid (0.58 g, 75%), NMR d CD3SOCD3) 2.34 (s, 3H), 3.75 (s, 3H), 3.85 (s, 3H), 6.99 (d, 1H), 7.19 (d, 1H), 7.29 (d, 1H), 11.93 (brs, 1H); M/z (+) 264 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed 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
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-150c8e9a5b574e7696c8d40be551101f
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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