Lithium hydroxide, monohydrate → 5-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acid

HRID 1515251Notes

Reaction equation

HRID 1515251 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][O:15]C(=O)C)=[CH:9][C:8]=2[N+:19]([O-:21])=[O:20])=[O:4].O.[OH-].[Li+]>O1CCCC1.CO.O>[OH:15][CH2:14][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([N+:19]([O-:21])=[O:20])[CH:9]=1)[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13]2

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 595429365-Acetoxymethyl-7-nitro-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 594480875-Hydroxymethyl-7-nitro-1H-indole-2-carboxylic acidYield 81.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Acetoxymethyl-7-nitro-1H-indole-2-carboxylic acid methyl ester (3.5 g, 12.0 mmol) prepared in Step B was dissolved in a solvent mixture of tetrahydrofuran, methanol and water (1:1:1, 100 mL). Lithium hydroxide hydrate (1.5 g, 35.9 mmol) was added thereto, and the mixture was stirred for 3 h at room temperature. After completion of the reaction, methanol and tetrahydrofuran were removed by distillation under reduced pressure. 1N hydrochloric acid was added to the residue. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by column chromatography to give the title compound (2.3 g, Yield 81%).

Workup

  1. customwere removed by distillation under reduced pressure
  2. addition1N hydrochloric acid was added to the residue
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8a5aea79c2634c8396a6cb56c7053d27
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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