Sodium Hydroxide → HCID 54710167, compound

HRID 1080643Notes

Reaction equation

HRID 1080643 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-6eb85823c6c042d3a25ee0279c77f33c
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

Loading…