Sodium Hydroxide → 5-Nitroindole-2-carboxylic acid

HRID 1829985Notes

Reaction equation

HRID 1829985 reaction equation
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][C:4]=1[C:15]([OH:17])=[O:16])C.[OH-].[Na+]>C(O)C>[N+:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]([C:15]([OH:17])=[O:16])=[CH:3]2)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 949984HCID 949984, compound

Product 1

HCID 3512915-Nitroindole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of commercial ethyl 5-Nitro-2-carboxy-indole (10.21 g, 43.6 mmol) in ethanol (220 mL) was added 110 mL of 2 M NaOH. The reaction was stirred at 60° C. for 18 hours. The reaction was then cooled and the ethanol removed in vacuo and then an additional 200 mL water was added. To the vigourously stirring aqueous solution was added 5 M HCl followed by 1 M HCl until pH 4 was attained and the acid product was precipitated. The product was collected by filtration on a Buchner funnel and washed once with dilute HCl (1:40 v/v) and twice with water. The filtrate was dried over P2O5 in a dessicator in vacuo to afford 8.83 g (42.8, 98%) of acid 97.

Workup

  1. temperatureThe reaction was then cooled
  2. customthe ethanol removed in vacuo
  3. additionan additional 200 mL water was added
  4. additionTo the vigourously stirring aqueous solution was added 5 M HCl
  5. customthe acid product was precipitated
  6. filtrationThe product was collected by filtration on a Buchner funnel
  7. washwashed once with dilute HCl (1:40 v/v) and twice with water
  8. dry with materialThe filtrate was dried over P2O5 in a dessicator in vacuo

Sources & evidence

ORD record
ord-a4f06e4e53304dbb81cd9b17d98d2903
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Reaction notes

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