Sodium Hydroxide → 3-Amino-2'-fluorobiphenyl-4-carboxylic acid

HRID 1811140Notes

Reaction equation

HRID 1811140 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66605809Methyl 3-amino-2'-fluorobiphenyl-4-carboxylate

Product 1

HCID 463144233-Amino-2'-fluorobiphenyl-4-carboxylic acidYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2 A solution of methyl 3-amino-2′-fluorobiphenyl-4-carboxylate (0.425 g, 1.73 mmol) in 1 M aqueous sodium hydroxide (6.9 mL, 6.9 mmol) and THF (3.5 mL) was heated at reflux overnight. The mixture was cooled to rt and concentrated almost to dryness. 6 M hydrochloric acid (0.1 mL) was added to the solution at 0° C. and the precipitate was collected by filtration, washed with water and dried to give 3-amino-2′-fluorobiphenyl-4-carboxylic acid (0.338 g, 84%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.87, d, 8.25, 1H), 7.50 (t, J=7.97, 1H), 7.47-7.55 (m, 1H), 7.25-7.36 (m, 2H), 6.92 (br s, 1H), 6.76 (s, 1H), 6.59 (d, J=7.70, 1H). Mass spectrum m/z 232.1 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated almost to dryness
  3. addition6 M hydrochloric acid (0.1 mL) was added to the solution at 0° C.
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-257ac390b7bd42a0b2015e3f833bf4da
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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