Hydrochloric Acid → 2-Carboxymethyl-5-(3-chlorophenoxy)-1-(4-diethylaminophenyl)indole-3-carboxylic acid

HRID 420954Notes

Reaction equation

HRID 420954 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH:13]=2)[N:8]([C:23]2[CH:28]=[CH:27][C:26]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[CH:25][CH:24]=2)[C:7]=1[CH2:34][C:35]([O:37]CC)=[O:36])=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[C:35]([CH2:34][C:7]1[N:8]([C:23]2[CH:24]=[CH:25][C:26]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])=[CH:27][CH:28]=2)[C:9]2[C:14]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][C:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)=[CH:11][CH:10]=2)([OH:37])=[O:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 666575815-(3-Chlorophenoxy)-1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-indole-3-carboxylic acid ethyl ester

Product 1

HCID 666577432-Carboxymethyl-5-(3-chlorophenoxy)-1-(4-diethylaminophenyl)indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-(3-chlorophenoxy)-1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-indole-3-carboxylic acid ethyl ester (100 mg, 0.18 mmol, see step (a) above), NaOH (1 M in methanol, 2 mL, 2.0 mmol), NaOH (aq, 1 M, 2 mL, 2.0 mmol) and dioxane (2 mL) was stirred at reflux for 4 h, cooled, acidified to pH 4 with HCl (aq, 1 M) and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography. Yield 50 mg (56%), mp 186-191° C.

Workup

  1. temperatureat reflux for 4 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-19d98418ad58406e95a9634240286324
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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