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Acetic Acid → 7-Nitro-1-oxo-2-(2-pyridylmethylidene)-1,2,3,4-tetrahydronaphthalene

HRID 7059
Notes
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Reaction equation

HRID 7059 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]=O.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[CH:21][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)[C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 142732-PyridinecarboxaldehydeHCID 384457-Nitro-1-tetralone

Product 1

HCID 696642877-Nitro-1-oxo-2-(2-pyridylmethylidene)-1,2,3,4-tetrahydronaphthaleneYield 19.1%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

7-Nitro-1-tetralone (500 mg), pyridine-2-aldehyde (315 mg), piperidine (0.15 ml) and acetic acid (0.4 ml) are dissolved in toluene (10 ml), and the mixture is heated under reflux for 12 hours. The reaction solution is washed with water, and the organic layer is dried over sodium sulfate. The solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 7-nitro-1-oxo-2-(2-pyridylmethylidene)-1,2,3,4-tetrahydronaphthalene (140 mg).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. washThe reaction solution is washed with water
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. customThe solvent is evaporated under reduced pressure
  6. customThe residue is purified by silica gel chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8189913a89c34604a80c6e562e94b274
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084176B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes