Pyridine → HCID 14517946, compound

HRID 476515Notes

Reaction equation

HRID 476515 reaction equation
[F:1][C:2]1[C:12]([NH:13][NH:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=[N:21][OH:22])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.N1C=CC=CC=1>O1CCCC1.O.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[C:12]([N:13]2[N+:21]([O-:22])=[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]3=[N:14]2)=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 1049PyridineHCID 86743538HCID 86743538, compound

Product 1

HCID 14517946HCID 14517946, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[2-(7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl)hydrazino]cyclohexanone oxime (3.0 g) in tetrahydrofuran (100 ml), 15% aqueous pyridine (60 g) was added, and a solution of copper sulfate (6 g) in water (10 ml) was added thereto, followed by heating at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 10% aqueous copper sulfate solution, dried and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate as an eluent to give 2-(7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl)-4,5,6,7-tetrahydro-1,2,3-benzotriazole-1-oxide. m.p., 219°-221° C.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 10% aqueous copper sulfate solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7a072476707646109cf939395748ca2c
Source dataset
uspto-grants-1989_12
Patent number
US04885024

Reaction notes

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