methyl 3-acetyl-6-chloro-1H-indole-5-carboxylate → 3-acetyl-6-chloro-1H-indole-5-carboxylic acid

HRID 1891019Notes

Reaction equation

HRID 1891019 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:17])=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2]>[OH-].[Na+].O1CCOCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:17])=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 67774875methyl 3-acetyl-6-chloro-1H-indole-5-carboxylate

Product 1

HCID 677727683-acetyl-6-chloro-1H-indole-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 3-acetyl-6-chloro-1H-indole-5-carboxylate (0.21 g, 0.84 mmol) in 1.5 N sodium hydroxide (0.7 mL) and dioxane (0.5 mL) was heated at 60 C for 6 h and stirred overnight at room temperature. The reaction was quenched by the addition of acetic acid and diluted with water. The resulting solid was filtered, washed with water and dried in vacuo to give the title compound (0.17 g, 96%) as pale yellow powder, m/z=238 (M+H).

Workup

  1. customThe reaction was quenched by the addition of acetic acid
  2. additiondiluted with water
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-16c9e3526619438c92b2f5f37701ded0
Source dataset
uspto-grants-2013_08
Patent number
US08507499B2

Reaction notes

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