Hydroxyamine hydrochloride → HCID 118005884, compound

HRID 1049627Notes

Reaction equation

HRID 1049627 reaction equation
Cl.[NH2:2]O.[Br:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([CH:16]=O)=[CH:10]2>CS(C)=O.C(OCC)(=O)C>[Br:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([C:16]#[N:2])=[CH:10]2

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 118005892HCID 118005892, compound

Product 1

HCID 118005884HCID 118005884, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Hydroxylamine hydrochloride (0.5 g, 7.9 mmol) was added to a solution of 32 (1.0 g, 4.0 mmol) in DMSO (5.0 mL), and the mixture was stirred for 16 h at 100° C. After cooling to room temperature, the mixture was diluted with ethyl acetate (100 mL), and washed with saturated NaHCO3 aqueous solution (2×50 mL). The organic was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation, and purified by column chromatography to give 5-bromo-7-fluoro-2-naphthonitrile (33) (28%). 1H NMR (400 MHz, CDCl3) δ 10.20 (s, 1H), 8.34 (d, J=8.8 Hz, 1H), 8.29 (s, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.77 (dd, J=8.0, 2.3 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H). GC-MS (ES) for C11H5BrFN [M+1]+ 250.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated NaHCO3 aqueous solution (2×50 mL)
  3. dry with materialThe organic was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-6597e09f328b42db86503f9d39bb2741
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

Loading…