Sodium Hydroxide → 7'-Bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

HRID 931596Notes

Reaction equation

HRID 931596 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:35])=[CH:9][C:10]([O:33][CH3:34])=[CH:11][C:12]=3[C:13]32[CH2:20][CH2:19][O:18][C:17]([NH:21]C(=O)C2C=CC([N+]([O-])=O)=CC=2)=[N:16]3)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:35])=[CH:9][C:10]([O:33][CH3:34])=[CH:11][C:12]=3[C:13]32[CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67439840N-(7'-bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthene]-2-yl)-4-nitrobenzamide

Product 1

HCID 584659317'-Bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amineYield 89.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of N-(7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2-yl)-4-nitrobenzamide (6.0 g, 11.06 mmol) in methanol (60 mL) was heated to 65° C. NaOH (2 M solution) (48.7 ml, 97 mmol) was added and the resulting mixture was heated to 65° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure, the precipitate was filtered off, washed twice with water and dried to afford 7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (3.90 g, 9.92 mmol, 50.9% yield) as white solid.

Workup

  1. temperaturethe resulting mixture was heated to 65° C. for 4 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationthe precipitate was filtered off
  4. washwashed twice with water
  5. customdried

Sources & evidence

ORD record
ord-50bf43408fba4d63a6c7661dcebd9470
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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