Ethanol → HCID 46701752, compound

HRID 1626411Notes

Reaction equation

HRID 1626411 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]=[N: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+].C(O)C>C1COCC1.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]=[N: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 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67288338HCID 67288338, compound

Product 1

HCID 46701752HCID 46701752, compoundYield 82.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(6-chloroquinoxalin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (540 mg, 1.00 mmol) was diluted with THF (8 mL) followed by the addition of NaOH (5015 μL, 5.02 mmol) and ethanol (4 mL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 0.5 M HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was triturated with DCM to provide the desired product (420 mg, 0.823 mmol, 82.1% yield). MS (ESI)=510.1 (M+1).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was triturated with DCM

Sources & evidence

ORD record
ord-c5ce0fcc88614d1e8cbef974ae06c44a
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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