Hydrochloric Acid → HCID 178474212, compound

Temperature

78 °C

N-[4-(2-Oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamide (1.15 g, 3.90 mmol) and ethyl formate (0.95 mL, 11.70 mmol) were dissolved in anhydrous ethanol (8.00 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (4.40 mL, 11.70 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 3 with dropwise addition of 1M HCl(aq). The dark orange precipitate that formed was filtered then re-dissolved in EtOH (25 mL). The ethanolic solution was made basic with the addition of 1 M NaOH(aq) (4 mL). The basic solution then was re-acidified to pH 1 with 1 M HCl(aq) (10 mL) causing the formation of a pale orange precipitate. This suspension was filtered yielding an orange solid as the pure N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamide (0.852 g, 2.64 mmol, 68%).

1. customproducing a black oil
2. temperatureSubsequently, the reaction mixture was cooled to room temperature
3. customThe dark orange precipitate that formed
4. filtrationwas filtered
5. dissolutionthen re-dissolved in EtOH (25 mL)
6. additionThe ethanolic solution was made basic with the addition of 1 M NaOH(aq) (4 mL)
7. filtrationThis suspension was filtered

ORD record

ord-1e000d66403d4efa926b60fb9ed2b73a

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07692005B2