Methanol → 2-Chloro-5,6-dimethylnicotinaldehyde

A mixture of 2-chloro-3-cyano-5,6-dimethylpyridine (21.5 g) semicarbazide hydrochloride (24.0 g), sodium acetate (42.3 g), water (225 ml) and methanol (475 ml) was hydrogenated at 344 kPa at 50° using Raney nickel catalyst (5 g). The mixture was added to water (750 ml) and filtered. The solid filtered off was suspended in water (130 ml) and concentrated hydrochloric acid (70 ml) was added and the mixture was heated at 100° for 1 hour, formalin (40% w/w, 120 ml) was added and the mixture was heated at 100° for a further 0.5 hour and allowed to cool. Sodium acetate (95 g) and water (250 ml) were added and the mixture was extracted with ether and the extracts were washed with 5% aqueous potassium carbonate and evaporated to give 2-chloro-5,6-dimethyl-3-pyridinecarboxaldehyde (13.24 g, 60%) m.p. 69°-70°.

1. customwas hydrogenated at 344 kPa at 50°
2. filtrationfiltered
3. filtrationThe solid filtered off
4. additionconcentrated hydrochloric acid (70 ml) was added
5. temperaturethe mixture was heated at 100° for 1 hour
6. additionformalin (40% w/w, 120 ml) was added
7. temperaturethe mixture was heated at 100° for a further 0.5 hour
8. temperatureto cool
9. additionSodium acetate (95 g) and water (250 ml) were added
10. extractionthe mixture was extracted with ether
11. washthe extracts were washed with 5% aqueous potassium carbonate
12. customevaporated

ORD record

ord-1782120f6fed4912a97a535f5967a625

Source dataset

uspto-grants-1980_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04234588