Chloride → 3-Formyl-1H-indole-5-carbonitrile

Phophoyl chloride (4.24 ml, 45.48 mmol) was added dropwise to dimethylformamide (3.52 ml, 45.48 mmol) and stirred for 30 mins at room temperature. A solution of 1H-indole-5-carbonitrile (5.39 g, 37.9 mmol) in dimethylformamide (10 ml) was added dropwise. A solid precipitated, further dimethylformamide (10 ml) was added to aid stirring and the reaction mixture was then stirred at room temperature for 3 hr. Water was s added to quench the reaction mixture which was then stirred for 18 hr. The stirring was stopped and the reaction mixture was left to stand, after 24 hr a pink solid had precipitated in the organic layer. The layers were separated and organic layer filtered, washed with water and dried to give the desired product (5.44 g, 84%). 1H NMR (DMSO) δ 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).

1. customA solid precipitated
2. additionfurther dimethylformamide (10 ml) was added to aid
3. stirringstirring
4. stirringthe reaction mixture was then stirred at room temperature for 3 hr
5. additionadded
6. customto quench the reaction mixture which
7. stirringwas then stirred for 18 hr
8. waitthe reaction mixture was left
9. waitto stand, after 24 hr
10. customa pink solid had precipitated in the organic layer
11. customThe layers were separated
12. filtrationorganic layer filtered
13. washwashed with water
14. customdried

ORD record

ord-6b404e5917454a8cb012bc49e79cc1f8

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06180627B2