Sodium Hydroxide → HCID 18452500, compound

HRID 1271064Notes

Reaction equation

HRID 1271064 reaction equation
[F:1][C:2]1[C:3]([NH:23][CH3:24])=[CH:4][C:5]2[O:10][CH2:9][N:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=3)[C:7](=[O:21])[C:6]=2[CH:22]=1.[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[C:3]([NH:23][CH3:24])=[CH:4][C:5]2[O:10][CH2:9][N:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=3)[C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18452519HCID 18452519, compound

Product 1

HCID 18452500HCID 18452500, compoundYield 421.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To methyl 4-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)benzoate (0.05 g, 0.15 mmol) was dissolved in dioxan (2 ml) and to it was added sodium hydroxide (0.012 g, 0.3 mmol) in water (0.5 ml) and the mixture stirred for 4 hr at room temperature. The solvent was removed under vacuum and the residue acidified, extracted with ethyl acetate (2×10 ml), dried over anhydrous sodium sulfate and concentrated to provide 4-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)benzoic acid (0.2 g, 41%). RP-HPLC: 1.8 min; ES-MS (M+H)+=317.0.

Workup

  1. customThe solvent was removed under vacuum
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ffea7f820f0f4adf9fab52768523e00e
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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