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Hexane → 1-(7-acetyl-9H-carbazol-2-yl)ethanone

HRID 337392
Notes
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Reaction equation

HRID 337392 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:20]([C:23]1[CH:28]=[C:27]([C:29](=[O:31])[CH3:30])[CH:26]=[CH:25][C:24]=1[C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:40])[CH3:39])=[CH:34][CH:33]=1)([O-])=O.CCCCCC>ClC1C=CC=CC=1Cl>[CH:36]1[C:37]2[NH:20][C:23]3[C:24](=[CH:25][CH:26]=[C:27]([C:29](=[O:31])[CH3:30])[CH:28]=3)[C:32]=2[CH:33]=[CH:34][C:35]=1[C:38](=[O:40])[CH3:39]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 712724381,1'-(2-Nitro-[1,1'-biphenyl]-4,4'-diyl)diethanone

Product 1

HCID 42891861-(7-acetyl-9H-carbazol-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

The mixture of triphenylphosphine (3.47 g, 13.24 mmol) and 1,1′-(2-nitro-[1,1′-biphenyl]-4,4′-diyl)diethanone (1.5 g, 5.30 mmol) in 1,2-dichlorobenzene (o-DCB) (15.90 mL) was heated at 180° C. under microwave irradiation for 1 h. The reaction mixture was cooled and poured in to the hexane (50 mL). Most of the impurities were removed by precipitation from hexane. The compound was further purified on silica gel ((0-100% EtOAc/Hexane). Fractions were concentrated to give the title compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customMost of the impurities were removed by precipitation from hexane
  3. customThe compound was further purified on silica gel ((0-100% EtOAc/Hexane)
  4. concentrationFractions were concentrated

Sources & evidence

ORD record
ord-1fcb01bcd9814ae29c81c42c04007f39
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889726B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes