Ammonium Chloride → Methyl 2-(2-amino-5-(piperidin-1-yl)phenyl)isonicotinate

Into a 100-mL round bottom flask, was placed a solution of methyl 2-(2-nitro-5-(piperidin-1-yl)phenyl)isonicotinate (1.8 g, 5.28 mmol, 1.00 equiv) in methanol (15 mL), and a solution of NH4Cl (850 mg, 15.89 mmol, 3.00 equiv) in water (7.9 mL). This was followed by the addition of iron (2.9 g, 51.79 mmol, 9.99 equiv) in several batches at 70° C. The resulting solution was stirred for 4 h at 70° C. in an oil bath. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 10 mL of water, extracted with 3×20 mL of ethyl acetate, and the organic layers combined. The resulting mixture was washed with 3×10 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in 1.4 g (85%) of methyl 2-(2-amino-5-(piperidin-1-yl)phenyl)isonicotinate as a black semi-solid.

1. customInto a 100-mL round bottom flask, was placed
2. filtrationThe solids were filtered out
3. concentrationThe resulting mixture was concentrated under vacuum
4. additionThe resulting solution was diluted with 10 mL of water
5. extractionextracted with 3×20 mL of ethyl acetate
6. washThe resulting mixture was washed with 3×10 mL of brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum
9. customThis resulted in 1.4 g (85%) of methyl 2-(2-amino-5-(piperidin-1-yl)phenyl)isonicotinate as a black semi-solid

ORDレコード

ord-c7695545de894982bd31d0ea0d301d43

出典データセット

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09301951B2