Hydrochloric Acid → 2-phenylpyridin-3-amine Hydrochloride

HRID 429517Notes

Reaction equation

HRID 429517 reaction equation
[ClH:1].[C:2]1([C:8]2[C:13]([NH:14]C(=O)C)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[ClH:1].[C:2]1([C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18356427N-(2-phenyl-pyridin-3-yl)-acetamide hydrochloride

Product 1

HCID 27627832-phenylpyridin-3-amine HydrochlorideYield 897.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(2-phenyl-pyridin-3-yl)-acetamide hydrochloride (61.9 g, 24.9 mmol) in tetrahydrofuran (100 mL) was added concentrated hydrochloric acid (100 mL). The reaction mixture was heated to reflux overnight and concentrated to a low volume. Tetrahydrofuran was added (2000 mL) and the volume was reduced to about 1000 mL as, product started precipitating. The mixture was cooled to 0° C. and was granulated for two) hours. The solids were filtered to afford 2-phenyl-3-aminopyridine hydrochloride (46.2 g, 90%). M. p.=226-1227° C. 1H NMR (300 MHz, CDCl3) δ6.35 (bs, 3), 7.61-7.74 (m, 6), 7.82 (dd, 1, J=1.4, 8.6), 8.05 (dd, 1, J=1.5, 5.4). Analysis calculated for C11H11CIN2: C, 63.93; H, 5.36; N, 13.55. Found: C, 63.64; H, 5.20; N, 13.49.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated to a low volume
  4. additionTetrahydrofuran was added (2000 mL)
  5. customstarted precipitating
  6. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-d4dcaf05799f4fa580f06251af6127d6
Source dataset
uspto-grants-2001_11
Patent number
US06316632B1

Reaction notes

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