Acetic Acid → 2-Diazo-1-(3-nitronaphthalen-1-yl)ethanone

HRID 1696488Notes

Reaction equation

HRID 1696488 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14](Cl)=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[N+:17](=[CH2:19])=[N-:18].CC(O)=O>C1COCC1>[N+:17](=[CH:19][C:14]([C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:15])=[N-:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550Diazomethane2×HCID 106574223-Nitro-1-naphthoyl chloride

Product 1

HCID 866116812-Diazo-1-(3-nitronaphthalen-1-yl)ethanoneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-nitro-napthalene-1-carbonyl chloride (8.4 g, 35.7 mmol) in anhydrous THF (70 mL) was added an ethereal solution of diazomethane (250 mL) dropwise at 0° C. The reaction mixture was stirred for 5 h, and then warmed to RT overnight. Excess diazomethane was decomposed by the dropwise addition of AcOH (50 mL). The mixture was extracted with Et2O (3×150 ml), washed with brine and saturated NaHCO3 aqueous solution, dried and filtered. The filtrate was concentrated to give the crude product, which was purified by column chromatography to yield 2-diazo-1-(3-nitronaphthalen-1-yl)ethanone (7.0 g, 81% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.14 (s, 1H), 8.47 (d, J=7.2 Hz, 1H), 8.35 (d, J=7.2 Hz, 1H), 8.35 (s, 1H), 7.84 (t, J=7.2 Hz, 2H), 7.76 (t, J=7.8 Hz, 2H), 6.84 (s, 1H); MS (ESI) m/z: 242 (M+H+).

Workup

  1. extractionThe mixture was extracted with Et2O (3×150 ml)
  2. washwashed with brine and saturated NaHCO3 aqueous solution
  3. customdried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-047c461bdc134eb2829e99acc605b664
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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