Sodium Hydroxide → HCID 12069598, compound

HRID 1716354Notes

Reaction equation

HRID 1716354 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[C:8]([C:10]1[N:18]2[C:13]([CH:14]=[CH:15][CH:16]=[CH:17]2)=[C:12]([C:19]([O:21]CC)=[O:20])[C:11]=1[CH3:24])=[O:9].CC1C(C(OCC)=O)=C2N(C=1)C=CC=C2>O1CCOCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[C:8]([C:10]1[N:18]2[C:13]([CH:14]=[CH:15][CH:16]=[CH:17]2)=[C:12]([C:19]([OH:21])=[O:20])[C:11]=1[CH3:24])=[O:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 594182HCID 594182, compoundHCID 12069566HCID 12069566, compound

Product 1

HCID 12069598HCID 12069598, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

26.2 ml of 1 N sodium hydroxide are added to 5 g (13.1 mmol) of ethyl 3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-1-ylcarboxylate, a compound of Example 13—prepared according to the procedure of Example 1 by benzoylation of ethyl (2-methylindolizin-1-yl)carboxylate described in J. Chem. Soc., (1963), pp. 3277-3280-, in suspension in 50 ml of dioxane, and the medium is heated under reflux for 17 hours. The reaction medium is concentrated under reduced pressure. The residue is taken up in water, washed with ethyl ether, and the medium is separated after settling out. The aqueous phase is acidified to pH 6 with a potassium hydrogen sulphate solution and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and concentrated under reduced pressure. 4.9 g of an orange-coloured powder are obtained.

Workup

  1. temperatureunder reflux for 17 hours
  2. concentrationThe reaction medium is concentrated under reduced pressure
  3. washwashed with ethyl ether
  4. customthe medium is separated
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbdad32429bb48b29a540dd31a5d17c7
Source dataset
uspto-grants-2010_09
Patent number
US07803811B2

Reaction notes

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