Hydrochloric Acid → HCID 18918281, compound

A solution of 4-dimethylaminopyridine-3-carboxaldehyde (J. Het. Chem, 25, 81) (1.5 g) in ethanol (25 ml) was treated with sodium borohydride (200 mg) and the mixture was stirred for 4 hours. Concentrated hydrochloric acid (1 ml) was added and the mixture was concentrated. The residue was treated with saturated aqueous sodium chloride (40m) and concentrated aqueous sodium hydroxide (2 ml) and the mixture was extracted with dichloromethane (4×20 ml). The combined organic extracts were washed with saturated aqueous sodium chloride (40 ml), dried (PS paper) and concentrated. The residue was dissolved in methanol, treated with decolourising charcoal, filtered and concentrated to give 4-dimethylaminopyridine-3-methanol (1.1 g) as a pale yellow oil. NMR: (d6DMSO): δ2.9 (6H,s); 4.5(2H,s); 4.0-4.8(1H, br.s); 6.7(1H,d); 8.15(1H,d); 8.3(1H,s); m/e 153 (M+H)+ ; 135(M+H-H2O)+.

1. concentrationthe mixture was concentrated
2. additionThe residue was treated with saturated aqueous sodium chloride (40m) and concentrated aqueous sodium hydroxide (2 ml)
3. extractionthe mixture was extracted with dichloromethane (4×20 ml)
4. washThe combined organic extracts were washed with saturated aqueous sodium chloride (40 ml)
5. customdried (PS paper)
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in methanol
8. additiontreated with decolourising charcoal
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-b70905abb8614340993b32c4ecfe9757

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563141