Water → 5-Amino-[1,1'-biphenyl]-2-carboxylic acid hydrochloride

HRID 2121168Notes

Reaction equation

HRID 2121168 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=1)([O-])=O.O.O.[Sn](Cl)[Cl:22].O.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[ClH:22].[NH2:1][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 106578414-Nitro-2-phenylbenzoic acid

Product 1

HCID 698924925-Amino-[1,1'-biphenyl]-2-carboxylic acid hydrochlorideYield 29.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Nitro-2-phenylbenzoic acid (10.5 g, 43.2 mmol) and tin(II) chloride dihydrate (34.1 g, 0.15 mol) were combined and refluxed in 250 mL ethyl acetate for 1 hour. An equal volume of water was added followed by solid NaHCO3 to pH 8. The mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine and concentrated to a thick oil. The oil was diluted with ether and excess anhydrous HCl was added. The resulting precipitate was collected and dried to provide 4-Amino-2-phenylbenzoic acid hydrochloride (3.2 g). MS m/e 214 (M+H)+. 1H NMR (d6-DMSO, 300 MHz) δ 6.65 (d, J=3 Hz, 1H), 6.79 (m, 1H), 7.20-7.72 (m, 6H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with brine
  3. concentrationconcentrated to a thick oil
  4. additionThe oil was diluted with ether and excess anhydrous HCl
  5. additionwas added
  6. customThe resulting precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-aa5cfd7e2ef542c9b2da901a454c4893
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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