Sodium Hydroxide → 6-nitro-1H-indole-2-carboxylic Acid

HRID 724537Notes

Reaction equation

HRID 724537 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[O:4].[OH-].[Na+]>CO>[N+:14]([C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([C:3]([OH:4])=[O:2])[NH:6]2)=[CH:11][CH:10]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11816863Methyl 6-nitro-1H-indole-2-carboxylate

Product 1

HCID 47149976-nitro-1H-indole-2-carboxylic AcidYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.4 g (20 mmol) 6-Nitro-1H-indole-2-carboxylic acid methyl ester (190) was dissolved in 80 mL methanol and was treated with 30 mL 1M NaOH overnight at 55 C°. The methanol was evaporated, the remaining aqueous solution was diluted to 100 mL and was acidified to pH 2 using concentrated HCl. The precipitate was filtered off, washed three times with water then dried to give 3.92 g (95%) 191 as yellow powder. The NMR was consistent with the structure. 191 was used without further purification.

Workup

  1. customThe methanol was evaporated
  2. additionthe remaining aqueous solution was diluted to 100 mL
  3. filtrationThe precipitate was filtered off
  4. washwashed three times with water
  5. customthen dried

Sources & evidence

ORD record
ord-b9e48dbd07354afeaca14050f1d6aff6
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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