Potassium tert-butoxide → HCID 90409706, compound

HRID 589053Notes

Reaction equation

HRID 589053 reaction equation
[CH3:1]C(C)([O-])C.[K+].[NH2:7][C:8]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:9]=1[O:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[N+:24]([C:23]1[CH:22]=[CH:21][CH:20]=[C:9]([O:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH2:1])[C:8]=1[NH2:7])([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 90409238HCID 90409238, compound

Product 1

HCID 90409706HCID 90409706, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (1.10 g, 9.9 mmol) was added to a suspension of methyl triphenylphosphonium bromide (3.0 g, 8 mmol) in tetrahydrofuran (30 mL) under nitrogen. The reaction was stirred at room temperature for 1 h, followed by addition of 2-(2-amino-3-nitrophenoxy)-1-pyridin-2-ylethanone (2 g, 8 mmol). The mixture was stirred for 3 h, and was then partitioned between water and ethyl ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. The product was purified by FCC on silica gel eluting with a hexane:ethyl acetate gradient to give 2-nitro-6-[(2-pyridin-2-ylprop-2-en-1-yl)oxy]aniline as light brown solid (0.5 g, 20%). LCMS calculated for C14H14N3O3 (M+H)+: m/z=272.1. found: 272.1.

Workup

  1. stirringThe mixture was stirred for 3 h
  2. customwas then partitioned between water and ethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe product was purified by FCC on silica gel eluting with a hexane

Sources & evidence

ORD record
ord-5ad8098b3dad4c0a82ea4074bf2225e0
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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