Ammonium Hydroxide → 9-Iminofluorene

HRID 878930Notes

Reaction equation

HRID 878930 reaction equation
Cl.[C:2]1(=N)[C:14]2[C:6]([C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:5][CH:4]=[CH:3]1.[NH4+:16].[OH-]>>[CH:2]1[C:14]2[C:13](=[NH:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 86652223HCID 86652223, compound

Product 1

HCID 205009-IminofluoreneYield 58%

Procedure

The fluorenone (4.0 g, 22.2 mmol) was stirred in an autoclave of 110° C. for three days in an ammonia atmosphere (7 to 8 atm). After the reaction, it was allowed to dissolve in diethyl ether. And, hydrogen chloride was blown into it. It was stirred for one hour at room temperature. The obtained suspension was filtered, and the filtrate was cleaned with the diethyl ether. With this, fluorenone imine hydrochloride (3.4 g, 71%) was obtained. This hydrochloride was allowed to decompose with an ammonia aqueous solution. And, it was recrystallized by using the methylene chloride and hexane. And, Fluoren-9-ylideneamine (2.3 g, 58%) was obtained.

Workup

  1. customAnd, it was recrystallized

Sources & evidence

ORD record
ord-4728682e94e14fcdacacc52c2489fb63
Source dataset
uspto-grants-2015_03
Patent number
US08987495B2

Reaction notes

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