Sodium Hydroxide → N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic Acid

HRID 1610925Notes

Reaction equation

HRID 1610925 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C(=O)C)=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([O:26]CC)=[O:25])=[CH:6][C:5]=1[C:29]#[C:30][Si](C)(C)C>CO.O.C(OCC)(=O)C.CCCC(C)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([OH:26])=[O:25])=[CH:6][C:5]=1[CH2:29][CH3:30]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 22259369ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate

Product 1

HCID 22259372N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic AcidYield 65.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 78922-MethylpentaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide (2M, 1.8 ml) was added to a solution of ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate (0.14 g) in methanol (5 ml) and the mixture was stirred for 3 hours. The methanol was removed and the residue obtained was diluted with water (20 ml) and extracted twice with ethyl acetate (20 ml each time). The aqueous layer was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (3×25 ml). The combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml) and dried (MgSO4). The residue obtained on removal of the solvent was dissolved in a mixture of ethyl acetate and iso-hexane (1:1) and passed down a 5 g silica Isolute column eluting with an ethyl acetate iso-hexane mixture (1:1) to give the title compound (65 mg). NMR (CD3SOCD3): d 4.5 (s, 1H), 5.7 (s, 2H), 6.8 (m, 1H), 6.9 (m, 2H), 7.1 (m, 1H), 7.2 (s, 1H), 7.35 (m, 1H), 7.4 (m, 2H), 9.0 (s, 1H); m/z 324.4 (M−H).

Workup

  1. customThe methanol was removed
  2. customthe residue obtained
  3. extractionextracted twice with ethyl acetate (20 ml each time)
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. washThe combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customThe residue obtained on removal of the solvent
  8. washeluting with an ethyl acetate iso-hexane mixture (1:1)

Sources & evidence

ORD record
ord-51ca09b46412458fae7bb2a7028d19d0
Source dataset
uspto-grants-2006_01
Patent number
US06984657B1

Reaction notes

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