Acetic Anhydride → 3'-Acetamido[1,1'-biphenyl]-4-carboxylic acid

HRID 1354779Notes

Reaction equation

HRID 1354779 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27563554-(3-aminophenyl)benzoic Acid

Product 1

HCID 200999843'-Acetamido[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3′-Aminobiphenyl-4-carboxylic acid (0.2 g) was mixed with pyridine (0.7 g) and acetic anhydride (180 mg) and, after 14 hours, volatile fractions were removed. The residue was taken up in sodium hydroxide solution (2N) and washed with diethyl ether. The aqueous phase was acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. This resulted in the product with the molecular weight of 255.28 (C15H13NO3); MS (ESI): 256 (M+H+).

Workup

  1. customvolatile fractions were removed
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThis resulted in the product with the molecular weight of 255.28 (C15H13NO3)

Sources & evidence

ORD record
ord-738835121b694eaeb42c5a3d3427156e
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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