Hydroxyamine hydrochloride → [1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-

HRID 1003756Notes

Reaction equation

HRID 1003756 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3OCCO3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.[NH2:21]O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:21])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 187986052-[p-(4-Methoxy phenyl)-phenyl]-1,3-dioxolane

Product 1

HCID 93892[1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-Yield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.6 g of 2-[p-(4-methoxy phenyl)-phenyl]-1,3-dioxolane, 0.917 g of hydroxylamine hydrochloride, 40 ml of 1.8 M hydrochloric ethanol and 10 ml of ethanol are introduced into a 100 ml three-necked flask under nitrogen. The reaction mixture is heated to reflux for 4 hours then concentrated under vacuum. The residue is taken up in 30 ml of water, then 220 ml of methyl ter-butyl ether (MTBE) is added. The organic phase is separated and the aqueous phase is extracted with MTBE (2×20 ml). The organic phases are combined, washed with a saturated solution of sodium chloride, dried over anhydrous magnesium sulphate and concentrated under vacuum (yield: 75%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4 hours
  3. concentrationthen concentrated under vacuum
  4. addition220 ml of methyl ter-butyl ether (MTBE) is added
  5. customThe organic phase is separated
  6. extractionthe aqueous phase is extracted with MTBE (2×20 ml)
  7. washwashed with a saturated solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulphate
  9. concentrationconcentrated under vacuum (yield: 75%)

Sources & evidence

ORD record
ord-c2bb1bb3709546a6ab44c1f58f4df6d6
Source dataset
uspto-grants-2000_04
Patent number
US06046352

Reaction notes

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