Hydrochloric Acid → HCID 178513245, compound

HRID 710440Notes

Reaction equation

HRID 710440 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:11][OH:12].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([C:1](=[NH:2])[NH:11][OH:12])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10340Sodium CarbonateHCID 12162Benzonitrile, 4-bromo-

Product 1

HCID 178513245HCID 178513245, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-cyano-bromobenzene (0.5 g, 2.75 mmol), HCl×NH2OH (0.476 g, 6.9 mmol) and Na2CO3 (0.731 g, 6.9 mmol) in a mixture of EtOH and H2O (25 ml: 5 ml) was stirred for 7 h at reflux. The solvent was evaporated to dryness and the residue was taken in EtOAc (100 ml) and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the product as colourless solid (0.51 g, 87%). 1H-NMR (DMSO-d6) 5.81 (broad s, 2H); 7.53 (d, 2H, J=6.66 Hz); 7.58 (d, 2H, J=6.54 Hz); 9.69 (s, 1H).

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated to dryness
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-369e3b23f28f4b889b8fc860bd8c712b
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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