Nitric Acid → HCID 58562961, compound

HRID 1186142Notes

Reaction equation

HRID 1186142 reaction equation
[F:1][C@H:2]1[CH2:8][O:7][CH2:6][C:5]([NH2:9])=[N:4][C@@:3]1([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])[CH3:10].[N+:18]([O-])([OH:20])=[O:19].[OH-].[Na+]>S(=O)(=O)(O)O>[F:1][C@H:2]1[CH2:8][O:7][CH2:6][C:5]([NH2:9])=[N:4][C@@:3]1([C:11]1[CH:16]=[C:15]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:13][C:12]=1[F:17])[CH3:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 58563136(5R,6R)-6-fluoro-5-(2-fluorophenyl)-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Product 1

HCID 58562961HCID 58562961, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of (5R,6R)-6-fluoro-5-(2-fluorophenyl)-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (1.2 mmol) in sulfuric acid (5.0 ml) was added at 0° C. red fuming nitric acid (1.9 mmol) over a period of 20 min and stirring was continued for 30 min. The solution was dropped slowly into ice/water (60 ml), the pH was adjusted to 9 by addition of aqueous 4 N NaOH and extracted with ethyl acetate. The organic layer was dried, evaporated and the residue purified by chromatography on silca-NH2 using n-heptane/ethyl acetate to give (5R,6R)-6-fluoro-5-(2-fluoro-5-nitro-phenyl)-5-methyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine as a pale yellow solid. MS (ISP): m/z=286.2 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. customevaporated
  4. customthe residue purified by chromatography on silca-NH2

Sources & evidence

ORD record
ord-676a41db9e6940249d036320847dba31
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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