Sodium Hydroxide → Indole-2-carboxylic acid

HRID 1677800Notes

Reaction equation

HRID 1677800 reaction equation
[OH-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([O:14]C)=[O:13]>CO.O>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70992Methyl 1H-indole-2-carboxylate

Product 1

HCID 72899Indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Add NaOH (82.0 mmol) to methyl indole-2-carboxylate 2 (27.0 mmol) as a suspension in MeOH/H2O (3:1, 160 mL). Stir at rt for 16 h, concentrate, and acidify with HCl. Collect the precipitate by filtration, wash with H2O and dry in vacuuo to afford indole-2-carboxylic acid 3.

Workup

  1. concentrationconcentrate
  2. customCollect the precipitate
  3. filtrationby filtration
  4. washwash with H2O
  5. customdry in vacuuo

Sources & evidence

ORD record
ord-20e922bfa5dc4a4c869081601d2304ba
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

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