Phosphinic Acid → 3-Methyl-1-(4-nitrophenyl)-7-methoxyisochroman

HRID 2179895Notes

Reaction equation

HRID 2179895 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[O:7][CH:6]([CH3:23])[CH2:5]2.N([O-])=O.[Na+].O[PH2]=O>OS(O)(=O)=O>[CH3:23][CH:6]1[CH2:5][C:4]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[CH:2][CH:3]=2)[CH:8]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[O:7]1

Participants

5

Reactant 3

HCID 4124402Phosphinic AcidHCID 224889636-Amino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochromanHCID 23668193Sodium Nitrite

Product 1

HCID 224889843-Methyl-1-(4-nitrophenyl)-7-methoxyisochromanYield 86%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Solution of 15 (100 mg, 0.32 mmol) in 5 ml of 4N H2SO4 was treated with NaNO2 (29.6 mg, 1.16 eq) at 0° C. for 15 min, followed by adding H3PO2 (50%, 0.25 ml) at such temperature. After refluxing for 5 hours, the solution was extracted with ethyl acetate three times. The combined organic phases were dried over Na2SO4. Removal of the solvent afforded the crude product. Purification of the crude product by using silica gel column gave the desired product 16 (82 mg, 86%).

Workup

  1. temperatureAfter refluxing for 5 hours
  2. extractionthe solution was extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customRemoval of the solvent
  5. customafforded the crude product
  6. customPurification of the crude product

Sources & evidence

ORD record
ord-55b7a71d521a435f8703b9b35bc0601b
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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