Hydrochloric Acid → HCID 3319455, compound

HRID 1880365Notes

Reaction equation

HRID 1880365 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13]CC)=[O:12])=[CH:7]2.[OH-].[K+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66920491HCID 66920491, compound

Product 1

HCID 3319455HCID 3319455, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 7-fluoro-4-methoxy-1H-indole-2-carboxylate (1.00 g, 4.22 mmol) in ethanol was added KOH (473 mg, 8.43 mmol). The reaction was stirred at room temperature for 12 hours, cooled to 0° C. and acidified with 1 N HCl. The mixture was extracted with EtOAc and CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the title compound (550 mg, 62%).

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe mixture was extracted with EtOAc and CH2Cl2
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-643b309e06cd4c3dbe12ac15b84ffd45
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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