Hydrochloric Acid → (2Z,4E)-5-(5,6-dichloro-1H-indol-2-yl)-2-methoxy-2,4-pentadienoic acid

HRID 1070697Notes

Reaction equation

HRID 1070697 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](/[CH:12]=[CH:13]/[CH:14]=[C:15](\[O:20][CH3:21])/[C:16]([O:18]C)=[O:17])=[CH:5]2.[OH-].[K+].CCO.CC(O)=O.Cl>CCO.O.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](/[CH:12]=[CH:13]/[CH:14]=[C:15](\[O:20][CH3:21])/[C:16]([OH:18])=[O:17])=[CH:5]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10806018methyl (2Z,4E)-5-(5,6-dichloroindol-2-yl)-2-methoxy-2,4-pentadienoateHCID 18476134Acetic acid ethanol

Product 1

HCID 22397576(2Z,4E)-5-(5,6-dichloro-1H-indol-2-yl)-2-methoxy-2,4-pentadienoic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A suspension of methyl (2Z,4E)-5-(5,6-dichloroindol-2-yl)-2-methoxy-2,4-pentadienoate (10 g, 30.7 mmol) and KOH (3.6 g, 64.2 mmol) in EtOH/water {fraction (1/1)} (460 ml) was refluxed for 3 h. The suspension after cooling to RT was poured into water (1.5 l), it was acidified with 2N HCl and extracted with AcOEt (2×1 l). The organic phase was washed with water and dried (MgSO4), then concentrated and the residue taken up with CH2Cl2. Filtration and drying in the oven at 50° produced 9.5 g of pure title compound (30.4 mmol, yield 99.1%), m.p.=249-250° C.

Workup

  1. temperaturewas refluxed for 3 h
  2. extractionextracted with AcOEt (2×1 l)
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationFiltration
  7. customdrying in the oven at 50°

Sources & evidence

ORD record
ord-97f6b8a382b34a5ea603eb6f193f8b31
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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