Hydrochloric Acid → HCID 22013535, compound

HRID 1995138Notes

Reaction equation

HRID 1995138 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1N.N(OCCC(C)C)=O.[ClH:23]>C(#N)C.[Cu](Cl)Cl>[Cl:23][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 6030842-amino-3-methylbiphenyl

Product 1

HCID 22013535HCID 22013535, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

During a five minute period a solution of 3-methyl-[1,1'-biphenyl]-2-amine (5.8 g, 0.0316 mole) in 15 ml of dry acetonitrile was added to a stirred mixture of anhydrous copper (II) chloride (7.5 g, 0.038 mole) and isoamyl nitrite (5.55 g, 0.0474 mole) in 100 ml of anhydrous acetonitrile. The reaction mixture was stirred at room temperature for two hours, 65° for two hours, then room temperature for two days. The mixture was diluted with 600 ml of 2 N aqueous hydrochloric acid and extracted with two 150 ml portions of diethyl ether. The extracts were combined, washed with 200 ml of 2 N aqueous hydrochloric acid, and dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to give an oil. The oil was purified by column chromatography on silica gel to give 2-chloro-3-methyl-[1,1'-biphenyl] (0.4 g).

Workup

  1. waitroom temperature for two days
  2. extractionextracted with two 150 ml portions of diethyl ether
  3. washwashed with 200 ml of 2 N aqueous hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give an oil
  8. customThe oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5c4117c4548e4f60a7ff3bebea2026b5
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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