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

HRID 2085885Notes

Reaction equation

HRID 2085885 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-f0de90887fc6439eb75507e227679399
Source dataset
uspto-grants-2004_04
Patent number
US06720351B2

Reaction notes

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