Carbon Dioxide → 1-Acetyl-5-chloroindoline

1428 g (12 moles) of indoline and 3000 ml of chloroform were admixed with stirring with 1350 g (132 moles) of acetic acid anhydride with cooling to keep the temperature at 20° to 30° C. and the mixture was stirred for one hour. Then, 600 ml of water were added thereto followed by addition in portions over 71/2 hours to the mixture of 702 g (6.6 moles) of sodium carbonate with vigorous stirring and external cooling during which carbon dioxide evolved. Within 7.5 hours 937 g (13.2 moles) of chlorine were added to the mixture held at no more than 30° C. and the mixture was stirred for 30 minutes. 3000 g of water were added to the mixture which was stirred for 15 minutes after which the organic phase was separated and evaporated to dryness under reduced pressure at 130° C. At 70° to 75° C. 2400 ml of isopropanol were added to the residue and the mixture was stirred with heating until total dissolution occured and the mixture was cooled to room temperature and was stirred at 20° to 25° C. for one hour. The mixture was vacuum filtered to obtain 5-chloro-1-acetyl-indoline melting at 115° to 116° C. which was washed with 1500 ml of isopropanol.

1. temperaturewith cooling
2. customat 20° to 30° C.
3. additionthereto followed by addition in portions over 71/2 hours
4. stirringwith vigorous stirring
5. customheld at no more than 30° C.
6. stirringthe mixture was stirred for 30 minutes
7. stirringwas stirred for 15 minutes after which the organic phase
8. customwas separated
9. customevaporated to dryness under reduced pressure at 130° C
10. customAt 70° to 75° C
11. addition2400 ml of isopropanol were added to the residue
12. stirringthe mixture was stirred
13. temperaturewith heating until total dissolution
14. stirringwas stirred at 20° to 25° C. for one hour
15. filtrationfiltered

ORDレコード

ord-0a28437230f54b5faa46d1930107136f

出典データセット

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04377699