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

HRID 41206Notes

Reaction equation

HRID 41206 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].C1COCC1.Cl>CO.O>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 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 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium hydroxide (32.6 mL, 65.19 mmol) was added to a stirred suspension of methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate (8 g, 21.73 mmol) dissolved in MeOH (42 mL) and THF (21 mL) at 0° C. The resulting suspension was stirred at room temperature for 1 h. MeOH (60 mL), THF (10 mL) and water (10 mL) were then added to help stirring. Upon completion, the reaction was cooled to 0° C. and HCl 2N was added to the suspension until pH 2. The solid was collected by filtration, washed with water, AcOEt, diethyl ether and dried with P205 under vacuum at 50° C. to give 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (7.0 g, 91%). Mass Spectrum: m/z [M+H]+=354.

Workup

  1. customat 0° C
  2. stirringto help stirring
  3. temperatureUpon completion, the reaction was cooled to 0° C.
  4. filtrationThe solid was collected by filtration
  5. washwashed with water, AcOEt, diethyl ether
  6. customdried with P205 under vacuum at 50° C.

Sources & evidence

ORD record
ord-e43fbff9e46c43a5a836cd5fefbc52b6
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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