Hydrochloric Acid → HCID 69588511, compound

N-Methyl-2-naphthalen-2-yl-acetamide (94 g, 470 mmol) and 71.3 g (71 ml) of ethyl isonicotinate (470 mmol) were partially dissolved in 800 mL of anhydrous THF in a 3 L, 3-necked r.b. flask equipped with a mechanical stir, temperature probe, and a 500-mL addition funnel. The flask was cooled to 0–5° C. in an ice-water bath. tBuOK (1M in THF, 470 mL) was added slowly into the heterogeneous mixture. After the addition, the resulting yellow-brown heterogeneous mixture was stirred overnight at RT. The resulting dark solution was cooled to 0–5° C. in an ice-water bath. Distilled water (800 mL) was added. The basic solution was neutralized to pH 7 using 37% HCl. The solvent was removed in vacuum at RT. The resulting solid was filtered off, washed by slurring in water (1 L) and toluene (1 L), respectively. The suspension was then filtered. The solid was dried under vacuum at 50° C. overnight and used crude in the next step.

1. customflask equipped with a mechanical stir, temperature probe, and a 500-mL addition funnel
2. temperatureThe flask was cooled to 0–5° C. in an ice-water bath
3. additionAfter the addition
4. temperatureThe resulting dark solution was cooled to 0–5° C. in an ice-water bath
5. customThe solvent was removed in vacuum at RT
6. filtrationThe resulting solid was filtered off
7. washwashed
8. filtrationThe suspension was then filtered
9. customThe solid was dried under vacuum at 50° C. overnight

ORD record

ord-01878d975a954a278abd0d88cc19cb80

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07026326B2