Lithium hydroxide, monohydrate → 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid

HRID 1058401Notes

Reaction equation

HRID 1058401 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][CH2:13][C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][NH:20]3)=[CH:16][CH:15]=2)=[O:11])=[CH:6][C:5]=1[Cl:23].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:23][C:5]1[CH:6]=[C:7]([C:10]([NH:12][CH2:13][C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][NH:20]3)=[CH:16][CH:15]=2)=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:24])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23560776HCID 23560776, compound

Product 1

HCID 186730192-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid methyl ester (Example 80; 2.00 g, 5.9 mmol) in tetrahydrofuran/methanol (1:1; 10 mL) was added to a solution of lithium hydroxide monohydrate (491 mg, 11.7 mmol) in water (5 mL). The solution was allowed to stir at room temperature for 72 h and then concentrated under reduced pressure to remove tetrahydrofuran and methanol. The remaining solution was diluted with water and acidified with 1N hydrochloric acid solution. The resulting mixture was extracted with ethyl acetate and the organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to afford 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid (1.90 g, 99% yield) as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove tetrahydrofuran and methanol
  3. additionThe remaining solution was diluted with water
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-298c86ba199d4479878d1ba8d69cf5ec
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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