ethyl-9',10'-difluoro-7'-oxospiro[cyclopentane-1,3'(2'H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6'-carboxylate → 9',10'-Difluoro-7'-oxo-2'H,7'H-spiro[cyclopentane-1,3'-[1,4]oxazino[2,3,4-IJ]quinoline]-6'-carboxylic acid

HRID 1396079Notes

Reaction equation

HRID 1396079 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:25])[C:8]2[CH:9]=[C:10]([F:24])[C:11]([F:23])=[C:12]3[O:17][CH2:16][C:15]4([CH2:21][CH2:20][CH2:19][CH2:18]4)[N:14]([CH:22]=1)[C:13]=23)=[O:5])C>C(O)(=O)C.O.OS(O)(=O)=O>[F:24][C:10]1[C:11]([F:23])=[C:12]2[O:17][CH2:16][C:15]3([CH2:21][CH2:20][CH2:19][CH2:18]3)[N:14]3[CH:22]=[C:6]([C:4]([OH:5])=[O:3])[C:7](=[O:25])[C:8]([CH:9]=1)=[C:13]23

Participants

3

Reactant 1

HCID 58134640ethyl-9',10'-difluoro-7'-oxospiro[cyclopentane-1,3'(2'H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6'-carboxylate

Product 1

HCID 581347029',10'-Difluoro-7'-oxo-2'H,7'H-spiro[cyclopentane-1,3'-[1,4]oxazino[2,3,4-IJ]quinoline]-6'-carboxylic acidYield 86.1%

Reagents, catalysts & solvents 1

HCID 86597087Acetic acid sulfuric acid waterSolvent

Procedure

A solution of ethyl-9′,10′-difluoro-7′-oxospiro[cyclopentane-1,3′(2′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (13.2 g, 38 mmol) in a mixture of acetic acid/water/H2SO4 (8:6:1 v/v, 75 mL) was heated under reflux for 2 h. The reaction mixture was poured into ice water. A precipitate formed and was collected by filtration, washed with water and then dried to give the title compound (10.5 g, 32.7 mmol, 86%) as a light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. customA precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-08535004d7c24fde80e8825ec495dc7b
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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