3-Aminobiphenyl → HCID 59737409, compound

HRID 1907715Notes

Reaction equation

HRID 1907715 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.Cl[C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]>C1COCC1.CCOC(C)=O>[C:1]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:2]=1

Participants

5

Reactant 2

HCID 167173-AminobiphenylHCID 4586585Methyl 8-chloro-8-oxooctanoate

Product 1

HCID 59737409HCID 59737409, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of biphenyl-3-amine (180) (0.171 g, 1.01 mmol) in THF (3 mL) was cooled to 0° C. then treated with methyl 8-chloro-8-oxooctanoate (181) and stirred for 2 h. The reaction mixture was then diluted with AcOEt, washed with saturated NH4Cl, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (eluent: 30 to 40% AcOEt in hexane), to provide title compound 182 (0.212 g, 69% yield).

Workup

  1. washwashed with saturated NH4Cl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (eluent: 30 to 40% AcOEt in hexane)

Sources & evidence

ORD record
ord-a1bedfaff408490ba0f787d7ff37213e
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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