1-Tetralone → 4-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide

HRID 2085688Notes

Reaction equation

HRID 2085688 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH:12][C:13](OC(C)(C)C)=O)=[C:7]([N+:20]([O-:22])=[O:21])[CH:6]=1)(=[O:4])=[O:3].[C:23]1(=O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30]C=2)[CH2:26][CH2:25][CH2:24]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)(C(F)(F)F)=O.ClCCl>[C:13]1(=[N:12]/[NH:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:6][C:7]=2[N+:20]([O-:22])=[O:21])/[CH2:30][CH2:29][CH2:28][C:27]2[C:32]/1=[CH:23][CH:24]=[CH:25][CH:26]=2

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22730367Tert-butyl 2-(4-(aminosulfonyl)-2-nitrophenyl)hydrazinecarboxylate

Product 1

HCID 96121654-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A room temperature solution of Example 73A (145 mg, 0.44 mmol) in 1:1 TFA/dichloromethane (10 mL) was stirred for 4 hours and concentrated. The concentrate was dissolved in ethanol (2 mL), treated with 3,4-dihydro-1(2H)-naphthalenone (8.2 mg, 0.06 mmol) and pyridinium p-toluenesulfonate (2 mg, 0.008 mmol), heated to reflux, stirred for 2 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 359 (M−H)−.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in ethanol (2 mL)
  3. temperatureheated
  4. temperatureto reflux
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-1ee27b8128354005a64871a52ea6d930
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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