Cyclohexane → HCID 21072275, compound

To a solution of 4-methylcyclohexanone (5.47 mL, 44.6 mmol), cyclohexane (70 mL) and glacial acetic acid (50 mL) was added 4-bromophenylhydrazine hydrochloride (10.0 g, 44.6 mmol) and the reaction mixture was refluxed for 23 h under a nitrogen atmosphere. The cooled reaction mixture was filtered and the filtrate was evaporated. Diethyl ether was added and the mixture was washed with a saturated sodium bicarbonate solution and then water; the ether solution was dried and evaporated. The crude product was recrystallised from ethanol over an ice bath, filtered, washed with cold PS and dried in vacuo to afford 6-bromo-3-methyl-1,2,3,4-tetrahydrocarbazole (8.73 g, 33.1 mmol, 74%) as an off-white solid, mp 108-110° C.

1. temperaturethe reaction mixture was refluxed for 23 h under a nitrogen atmosphere
2. customThe cooled reaction mixture
3. filtrationwas filtered
4. customthe filtrate was evaporated
5. additionDiethyl ether was added
6. washthe mixture was washed with a saturated sodium bicarbonate solution
7. dry with materialthe ether solution was dried
8. customevaporated
9. customThe crude product was recrystallised from ethanol over an ice bath
10. filtrationfiltered
11. washwashed with cold PS
12. customdried in vacuo

ORD record

ord-5209612fa7f248f7a8e300b7ca98c6c3

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612036B2