Hydrochloric Acid → HCID 66657612, compound

HRID 420908Notes

Reaction equation

HRID 420908 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][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:13]=2)[N:8]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:7]=1[CH2:33][C:34]([O:36]CC)=[O:35])=[O:5])C.[OH-].[Na+].O1CCOCC1.Cl>O>[C:34]([CH2:33][C:7]1[N:8]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=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:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=1)=[CH:11][CH:10]=2)([OH:36])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 66657600HCID 66657600, compound

Product 1

HCID 66657612HCID 66657612, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(4-chlorophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid ethyl ester (140 mg, 0.25 mmol, see step (c) Example 2), NaOH (aq, 2M, 2 mL) and dioxane (2 mL) were heated at 120° C. for 4.5 h, cooled, diluted with H2O, acidified to pH 2 with HCl (aq, 1 M) and extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was treated with CH2Cl2 (2 mL) to give the title compound as a white solid which was recrystallised from CH2Cl2/EtOH (9:1). Yield 45 mg (37%), mp 974-276° C.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. additionThe residue was treated with CH2Cl2 (2 mL)

Sources & evidence

ORD record
ord-cf03a0f6b89946c8bfc8357d3a008c11
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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