2-Aminobiphenyl → 2-Acetamidobiphenyl

HRID 718736Notes

Reaction equation

HRID 718736 reaction equation
O.[OH-].[Li+].[C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([NH2:10])=[CH:6][CH:7]=[CH:8][CH:9]=1.[C:17](Br)(=[O:19])[CH3:18]>C(Cl)Cl>[C:4]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:17](=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 70152-AminobiphenylHCID 10482Acetyl bromideHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 164472-AcetamidobiphenylYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Lithium hydroxide monohydrate (600 mg, 25.0 mmol) was added to a solution of the amine 3 (1.44 g, 8.53 mmol) dissolved in CH2Cl2 (125 mL) at 0° C. A solution of acetyl bromide (1.97 mL, 25.6 mmol) in CH2Cl2 (10 mL), was added dropwise over 5 minutes at 0° C. to the reaction mixture which was then allowed to warm to ambient temperature and stirred for 2 hours. The reaction crude was filtered, concentrated under reduced pressure, and purified by flash chromatography over silica, eluting with a gradient of 100% CH2Cl2 to 10% MeOH/90% CH2Cl2, yielding product 4 as white solid (1.11 g, 61.5%).

Workup

  1. customThe reaction crude
  2. filtrationwas filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography over silica
  5. washeluting with a gradient of 100% CH2Cl2 to 10% MeOH/90% CH2Cl2

Sources & evidence

ORD record
ord-87b53562334d4c53820e0f3b6c108f75
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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