Hydrochloric Acid → 4-(Phenylmethyl)-2-pyridinamine
Reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2-:14].[Na+].CC1C=CC(C(C)C)=CC=1.Cl>CCOC(C)=O.O>[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 165 °C
Procedure
A mixture of 4-benzylpyridine (14.1 mL, 88.6 mmol), sodium amide (5.71 g, 146 mmol), and p-cymene (105 mL) was heated to 165° C. After 1 d, the mixture was allowed to cool; water (30 mL) and concentrated hydrochloric acid (30 mL) were sequentially added, the aqueous layer was separated, and the organic layer was extracted with 60 mL of 2N HCl (aq). The aqueous extracts were then combined, washed with ether (50 mL), and made strongly basic with solid potassium hydroxide, during which time a brown oil separated. The oil was extracted into DCM (2×150 mL). The combined extracts were then dried over sodium sulfate, filtered, and concentrated to give a brown oil. Column chromatography (ISCO, 80 g, 50->100% EtOAc/Hex) afforded 4-benzylpyridin-2-amine as a tan solid. MS (ESI) m/z: Calculated: 184.1; Observed: 185 (M++1).
Workup
- temperatureto cool
- customthe aqueous layer was separated
- extractionthe organic layer was extracted with 60 mL of 2N HCl (aq)
- washwashed with ether (50 mL)
- customseparated
- extractionThe oil was extracted into DCM (2×150 mL)
- dry with materialThe combined extracts were then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give a brown oil
Sources & evidence
- ORD record
- ord-e0679635cf704fcea9877c44d0cbc42c
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919519B2
Reaction notes
Loading…