Hydrochloric Acid → 2-Amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acid

HRID 535456Notes

Reaction equation

HRID 535456 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([Br:25])[C:17]=2[CH3:26])=[O:15])=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].Cl>CO>[NH2:3][C:4]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([Br:25])[C:17]=2[CH3:26])=[O:15])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57500395Methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate

Product 1

HCID 666531732-Amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.92 ml (4.92 mmol) of a 1N aqueous solution of sodium hydroxide are added, at ambient temperature, to 1.91 g (4.69 mmol) of methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate in 30 ml of methanol. The reaction medium is refluxed for 10 hours and then hydrolysed with a 1N aqueous solution of hydrochloric acid. The aqueous phase is extracted with ethyl acetate. The organic phase obtained is washed with water, dried over sodium sulphate, filtered, and concentrated under reduced pressure. The solid obtained is rinsed with diisopropyl ether and dichloromethane, and dried under reduced pressure overnight at 50° C. 1.55 g of a yellow solid are obtained.

Workup

  1. temperatureThe reaction medium is refluxed for 10 hours
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. customThe organic phase obtained
  4. washis washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid obtained
  9. washis rinsed with diisopropyl ether and dichloromethane
  10. customdried under reduced pressure overnight at 50° C

Sources & evidence

ORD record
ord-a40eb93d44604b228e910ad53f99cc34
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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