Hydrochloric Acid → HCID 58993706, compound

HRID 391430Notes

Reaction equation

HRID 391430 reaction equation
N[C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.N(OC(C)(C)C)=O.[ClH:25].CO>C(#N)C.[Cu](Cl)Cl>[Cl:25][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 10906Tert-Butyl nitriteHCID 58993507HCID 58993507, compound

Product 1

HCID 58993706HCID 58993706, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of 3′-amino-5′-(hydroxymethyl)biphenyl-4-carbonitrile (120 mg, 0.54 mmol) in dry acetonitrile (1 mL) was added dropwise to a solution of copper (II) chloride (86 mg, 0.64 mmol) and tert-butyl nitrite (91 μL, 0.78 mmol) in acetonitrile (2 mL) at 65° C. After stirring for 30 min at 65° C., the reaction mixture was cooled to room temperature, poured into a 1 N hydrochloric acid solution, and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (20% ethyl acetate/hexanes) afforded 46 mg (35%). LC/MS: tR=2.54 min, 244.03 (MH)+. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=4 min., Flow rate=4 mL/min.).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×)
  3. washwashed with brine (2×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography on silica gel (20% ethyl acetate/hexanes) afforded 46 mg (35%)

Sources & evidence

ORD record
ord-3b3f6827f1e8460ab0ac5990fe9c3474
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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