Isatin → HCID 3661139, compound

Temperature

5 °C

To a solution of isatin (7.35 g) in N,N-dimethylformamide (70 ml) was added potassium tert-butoxide (6.98 g) under cooling at 5° C., and the reaction mixture was stirred for 10 minutes at the same temperature. To the mixture was added dropwise a solution of 1,4-dibromobutane (54 g) in N,N-dimethylformamide (25 ml), and stirred for an hour at 18° C. The reaction mixture was poured into ice-water, and extracted with chloroform. The extracts were combined, washed with water and evaporated. After addition of n-hexane (200 ml) to the residue, the solvent was decanted and then to the residue was added chloroform (20 ml). The mixture was filtered to remove insoluble substances and the filtrate was subjected to column chromatography on silica gel (50 g), eluted with chloroform. The fractions containing the object compound were collected, and concentrated to give dark red oil of 1-(4-bromobutyl)isatin (7.52 g).

1. stirringstirred for an hour at 18° C
2. extractionextracted with chloroform
3. washwashed with water
4. customevaporated
5. additionAfter addition of n-hexane (200 ml) to the residue
6. customthe solvent was decanted
7. additionto the residue was added chloroform (20 ml)
8. filtrationThe mixture was filtered
9. customto remove insoluble substances
10. washeluted with chloroform
11. additionThe fractions containing the object compound
12. customwere collected
13. concentrationconcentrated

ORD record

ord-42bce82a9d364ac0bd9f19dbd2bd0017

Source dataset

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04382934