Sodium Hydroxide → HCID 67287361, compound

HRID 1626414Notes

Reaction equation

HRID 1626414 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:32])[NH:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([Cl:31])[CH:27]=4)[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([O:35]CC)=[O:34].[OH-].[Na+]>C1COCC1.C(O)C.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:32])[NH:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([Cl:31])[CH:27]=4)[N:22]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([OH:35])=[O:34]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 67290661HCID 67290661, compound

Product 1

HCID 67287361HCID 67287361, compoundYield 78.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To ethyl 6-chloro-7-(4-(6-chloroquinolin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (1.31 g, 2.44 mmol) in THF (12 mL) and ethanol (6 mL) was added NaOH (6.09 mL, 12.2 mmol) and the reaction stirred at ambient temperature for 3 hours. The reaction was diluted with ethyl acetate (25 mL) and 1N aqueous HCl (20 mL). THF was added as needed to keep the organic layer clear. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated. The residue was triturated with DCM and the resulting solids were collected by filtration to provide the desired product (0.98 g, 1.92 mmol, 78.9% yield). MS (APCI)=509.0 (M+1).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with DCM
  6. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-407f76b96b174b748ba8bbaebfd18e17
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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