Hydrochloric Acid → HCID 86663005, compound

HRID 2410675Notes

Reaction equation

HRID 2410675 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.Cl.N([O-])=O.[Na+].[N-:31]=[N+:32]=[N-].[Na+]>C(O)C>[N:1]([C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[N+:31]=[N-:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 66604498HCID 66604498, compound

Product 1

HCID 86663005HCID 86663005, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4′-Amino-4,4″-dimethoxy-[1,1′:3′,1″-terphenyl]-5′-carbonitrile (226 mg, 0.68 mmol) was heated in ethanol (28 mL) to bring most of the material into solution. After cooling to room temperature, 17% aqueous HCl (4 mL) was added and the reaction was cooled in an ice bath. Sodium nitrite (76 mg, 1.09 mmol) was added and the orange-red solution was stirred for 15 min in the ice bath. Sodium azide (71 mg, 1.09 mmol) was then added. After 20 min, the reaction was partitioned between ethyl acetate and sufficient saturated aqueous sodium bicarbonate to neutralize the reaction. The organic phase was separated, washed with brine, and dried with sodium sulfate. Silica gel radial chromatograph using step gradient elution with hexane containing 5 to 20% ethyl acetate afforded 4′-azido-4,4″-dimethoxy-[1,1′:3′,1″-terphenyl]-5′-carbonitrile (108 mg, 44%) as a solid. 1H NMR (500, CDCl3) δ ppm 7.72 (1H, d, J=2.14 Hz), 7.62 (1H, d, J=2.14 Hz), 7.47 (2H, d, J=8.55 Hz), 7.39 (2H, d, J=8.55 Hz), 7.01 (2H, d, J=8.55 Hz), 6.97 (2H, d, J=8.85 Hz), 3.87 (3H, s), 3.84 (3H, s).

Workup

  1. temperaturethe reaction was cooled in an ice bath
  2. customthe reaction was partitioned between ethyl acetate and sufficient saturated aqueous sodium bicarbonate
  3. customthe reaction
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. washstep gradient elution with hexane containing 5 to 20% ethyl acetate

Sources & evidence

ORD record
ord-f67e83a64f15425fb1193a390a1c1a4c
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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