Hydrochloric Acid → Biphenyl

HRID 636255Notes

Reaction equation

HRID 636255 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12](C)=[CH:11][CH:10]=1)#N.NN.N([O-])=O.[Na+].Cl>C(O)C>[C:4]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 1455122-Cyano-4'-methylbiphenylHCID 23668193Sodium Nitrite

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 26.9 mmol of 2-cyano-4′-methyl-1,1′-biphenyl was dissolved in 150 ml of ethanol, and 270 mmol of hydrazine and 77.7 nmuol of 28% methylate were added thereto, followed by keeping at 50° C. for 48 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in 100 ml of ethanol, and 55 mmol of sodium nitrite and 110 mmol of concentrated hydrochloric acid were added to the solution at 0° C. After keeping at 0-5° C. for 2 hours, the reaction mixture was concentrated to give 2-(tetrazol-5-yl)-4′-methyl-1, I′-biphenyl. Yield, 46%

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 100 ml of ethanol
  3. waitAfter keeping at 0-5° C. for 2 hours
  4. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f75801fa9a6548b5b58924f67ab28bcc
Source dataset
uspto-grants-2001_02
Patent number
US06191289B1

Reaction notes

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