Water → HCID 12069591, compound

HRID 1716359Notes

Reaction equation

HRID 1716359 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH3:32])=[C:12]([C:19](=[O:31])[C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([O:29][CH3:30])[CH:21]=2)[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2)(=O)C.O.C(OCC)(=O)C>O1CCOCC1>[OH:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH3:32])=[C:12]([C:19]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([O:29][CH3:30])[CH:21]=2)=[O:31])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12069590HCID 12069590, compound

Product 1

HCID 12069591HCID 12069591, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.52 ml of 1 N sodium hydroxide are added to 420 mg (1.02 mmol) of 2-{[3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-1-yl]oxy}ethyl acetate, a compound of Example 79, dissolved in 6 ml of dioxane, and the medium is stirred at room temperature for 6 hours. The reaction medium is poured over water and ethyl acetate. The organic phase is separated after settling out, washed with water, dried over sodium sulphate and concentrated under reduced pressure. 340 mg of an orange-coloured powder are obtained, which powder is used without further purification in the subsequent nitro reduction step.

Workup

  1. customThe organic phase is separated
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92fa18d154a24a5db4df25c8ee593b1f
Source dataset
uspto-grants-2010_09
Patent number
US07803811B2

Reaction notes

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