Hydrochloric Acid → 1-(3-Nitrobenzyl)indole-5-carboxylic acid

HRID 2081698Notes

Reaction equation

HRID 2081698 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O-:3])=[O:2].[OH-].[Na+].Cl>O1CCCC1.CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19780394Methyl 1-[(3-nitrophenyl)methyl]-1H-indole-5-carboxylate

Product 1

HCID 197804001-(3-Nitrobenzyl)indole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the methyl ester (Example 1) (12.5 g) in tetrahydrofuran (150 ml) and methanol (300 ml) was added 2N sodium hydroxide (78 ml). The reaction mixture was heated under reflux for 4 hours, then cooled. The volume was reduced in vacuo to approximately 100 ml. and the solution acidified with 5N hydrochloric acid. On cooling, the crystalline product was filtered off and dried in vacuo in the oven at 50° C. to give 1-(3-nitrobenzyl)indole-5-carboxylic acid (m.p. 251°-254° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. temperatureOn cooling
  5. filtrationthe crystalline product was filtered off
  6. customdried in vacuo in the oven at 50° C.

Sources & evidence

ORD record
ord-d4bdf96320464f8a95b0a50e0e314341
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

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