Hydrochloric Acid → 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

HRID 41201Notes

Reaction equation

HRID 41201 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:21]([O:23]C)=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:10][C:9]2=[O:20].Cl>CO.C(Cl)Cl>[Br:3][C:4]1[CH:5]=[C:6]([C:21]([OH:23])=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:10][C:9]2=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58234996methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 582350518-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

NaOH 2N (40.7 mL, 81.48 mmol) was added to methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate (10 g, 27.2 mmol) in a mixture of methanol (225 mL) and DCM (75 mL). The slurry was stirred at room temperature for 16 h. The solvents were evaporated, water (150 mL) was added to the slurry, the solution was cooled down to 0° C. and HCl 6N (15 mL, 89.6 mmol) solution was added dropwise to the reaction mixture until pH ˜3.4. The formed solid was collected by filtration, washed with water (3×50 mL), then toluene (3×50 mL) followed by Diethyl ether (3×50 mL), dried at 55° C. under vacuum over P2O5 to afford 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (9.47 g, 98%) as a beige solid. The crude product was used without further purification.

Workup

  1. customThe solvents were evaporated
  2. additionwater (150 mL) was added to the slurry
  3. temperaturethe solution was cooled down to 0° C.
  4. filtrationThe formed solid was collected by filtration
  5. washwashed with water (3×50 mL)
  6. dry with materialdried at 55° C. under vacuum over P2O5

Sources & evidence

ORD record
ord-de74d1c0ecc94647be6e640c15ca8706
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

Loading…