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

HRID 1394827
Notes
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Reaction equation

HRID 1394827 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

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 1N 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-dd59cf149a8d4085bc53081ee956881e
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348355B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes