Methyl 3-(4-nitrophenyl)cyclobutane-1-carboxylate → Methyl 3-(4-aminophenyl)cyclobutane-1-carboxylate

HRID 2420142Notes

Reaction equation

HRID 2420142 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:13]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 20313166Methyl 3-(4-nitrophenyl)cyclobutane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 20313167Methyl 3-(4-aminophenyl)cyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of this nitro compound (750mg.) in ethyl acetate (20ml.) was stirred for 16 hours with a 5% palladium on carbon catalyst (250mg.) in an atmosphere of hydrogen. The solution was filtered through a pad of "Hyflo" and evaporated to give methyl 3-(4-aminophenyl)cyclobutanecarboxylate. A solution of this amine (800mg.) in dry benzene (20ml.) was stirred under argon at room temperature during the dropwise addition of amyl nitrite (0.755ml.). The temperature of the reaction mixture was slowly (over 21/2 hours) raised to its boiling point and the mixture was then refluxed for 1 hour. The solvent was evaporated under reduced pressure and the residue was chromatographed on a dry column of silica gel `MFC` (supplied commercially by Hopkin and Williams) (25g.), eluting with toluene to give a mixture of cis and trans isomers of methyl 3-(4-biphenylyl)cyclobutanecarboxylate, RF = 0.70 (9:1 v/v toluene/ethyl acetate). The n.m.r. spectrum in deuteriochloroform showed the following characteristic features (δ values):

Workup

  1. filtrationThe solution was filtered through a pad of "Hyflo"
  2. customevaporated

Sources & evidence

ORD record
ord-0581ca9f827b45d2b33d131514772ad1
Source dataset
uspto-grants-1978_08
Patent number
US04109015

Reaction notes

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