Sodium Hydroxide → HCID 54710167, compound

HRID 1598544Notes

Reaction equation

HRID 1598544 reaction equation
P(Cl)(Cl)Cl.[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[C:14]([C:17]1[C:29](=[O:30])[N:25]2[CH2:26][CH2:27][O:28][C:23]3[C:24]2=[C:19]([CH:20]=[CH:21][CH:22]=3)[C:18]=1[OH:31])([OH:16])=O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[OH:31][C:18]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:24]=2[N:25]([CH2:26][CH2:27][O:28]3)[C:29](=[O:30])[C:17]=1[C:14](=[O:16])[N:6]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[CH3:5]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 680244-Fluoro-N-methylanilineHCID 54710164HCID 54710164, compound

Product 1

HCID 54710167HCID 54710167, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Phosphorus trichloride (0.353 ml) was added dropwise to a water-cooled solution of N-methyl-4-fluoroaniline (3.04 g) in toluene (18 ml). The mixture was stirred at room temperature for 30 minutes. 6-Carboxy-2,3-dihydro-7-hydroxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (2 g) was added thereto, and the resulting mixture was stirred at 100° C. for 2 hours. Water (20 ml) and 4N sodium hydroxide (15 ml) were added thereto. The insoluble material was filtered and the filtrate was separated. The aqueous layer was acidified with hydrochloric acid and extracted with chloroform. The extract was dried over magnesium sulfate, filtered, and concentrated. The residue was recrystallized from a mixture of ethanol and isopropyl ether to give pale brown crystals of 2,3-dihydro-7-hydroxy-6-[N-(4-fluorophenyl)-N-methylcarbamoyl]-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (2.1 g).

Workup

  1. stirringthe resulting mixture was stirred at 100° C. for 2 hours
  2. filtrationThe insoluble material was filtered
  3. customthe filtrate was separated
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from a mixture of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-e1b08946053e435e98ffce2175b7a814
Source dataset
uspto-grants-1998_04
Patent number
US05739130

Reaction notes

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