Methanol → 3-(Aminomethyl)biphenyl

HRID 2080040

Reaction equation

HRID 2080040 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[N:8])[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[Cl-].[NH4+]>O1CCCC1.O>[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 34340[1,1'-Biphenyl]-3-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 27603683-(Aminomethyl)biphenylYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Next, a solution of the resulting biphenyl-3-carbonitrile (821 mg, 4.58 mmol) in tetrahydrofuran (5 mL) was added to a solution of lithium aluminum hydride (0.435 g, 11.5 mmol) in tetrahydrofuran (5 mL) that had been cooled on an ice bath, and the solution was stirred for 6 hours at room temperature. The reaction solution was cooled on an ice bath, a mixture solution of methanol and water (9:1) was added thereto, an aqueous solution of saturated ammonium chloride was further added, filtration was carried out through Celite pad and insoluble matter was removed. The filtrate was partitioned, the organic layer was dried over anhydrous magnesium sulfate, and the title compound (527 mg, 63%) was obtained as a brown oil. This was used in the next reaction without further purification.

Workup

  1. temperaturehad been cooled on an ice bath
  2. temperatureThe reaction solution was cooled on an ice bath
  3. filtrationfiltration
  4. customwas removed
  5. customThe filtrate was partitioned
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-b88dda3d777f4934bedbbbac1270a1ca
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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