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

HRID 2426726Notes

Reaction equation

HRID 2426726 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-d802fe5c72d144c09f9dcb5b8921f9f1
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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