HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 3-(Ethylamino)-8-fluoro-1,2,3,4-tetrahydrocarbazole 3-Acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole

HRID 427169
Notes
Print preview

Reaction equation

HRID 427169 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].Cl.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20]N.Cl>C(O)C>[C:1]([NH:4][CH:5]1[CH2:10][C:9]2[C:16]3[C:15](=[C:14]([F:13])[CH:19]=[CH:18][CH:17]=3)[NH:20][C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[CH2:1]([NH:4][CH:5]1[CH2:10][C:9]2[C:16]3[C:15](=[C:14]([F:13])[CH:19]=[CH:18][CH:17]=3)[NH:20][C:8]=2[CH2:7][CH2:6]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 538565N-(4-Oxocyclohexyl)acetamideHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

Product 1

HCID 234702853-(Ethylamino)-8-fluoro-1,2,3,4-tetrahydrocarbazole 3-Acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 7.8 g. of 4-acetamidocyclohexanone and 8.1 g. of 2-fluorophenylhydrazine hydrochloride in 75 ml. of absolute ethyl alcohol and 25 ml. of 5-N hydrogen chloride in absolute ethyl alcohol was heated under reflux for two hours, cooled, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and adsorbed on a column of aluminum oxide. Dilution with ether yielded first a small amount of side-product followed by the desired product which was recrystallized by dissolving in methyl alcohol, adding toluene, and evaporation of the methyl alcohol, to give 10.5 g. of 3-acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 202°-204° C.

Workup

  1. temperatureunder reflux for two hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in chloroform
  6. customDilution with ether yielded first a small amount of side-product

Sources & evidence

ORD record
ord-d935b22c7ab44529aa7e7fea5d41d246
Source dataset
uspto-grants-1979_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04172834

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes