Methanol → 5-(2-Hydroxy-benzoylamino)-1-methyl-1H-indole-2-carboxylic acid

HRID 490010Notes

Reaction equation

HRID 490010 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:28])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23]C(=O)C)=[CH:10][CH:9]=2)=[O:5])C.CO.O.[OH-].[Li+]>C1COCC1>[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:28])[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 691950055-(2-Acetoxy-benzoylamino)-1-methyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 222627095-(2-Hydroxy-benzoylamino)-1-methyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step (a) (2.0 g, 5.26 mM) was dissolved in THF (30 mL), methanol (10 mL), and water (10 mL). The mixture was treated with lithium hydroxide (882 mg, 21.04 mM) and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated to 15 mL and the pH was adjusted to about 3.0 with 1 N HCl. The mixture was extracted 3 times with ethyl acetate (25 mL). The ethyl acetate fractions were combined, dried over MgSO4, filtered and concentrated to provide the title compound.

Workup

  1. concentrationThe mixture was concentrated to 15 mL
  2. extractionThe mixture was extracted 3 times with ethyl acetate (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc0d59ff74524583b5cf8bff1f8ad2fc
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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