Sodium Nitrite → HCID 54059198, compound

HRID 1493643Notes

Reaction equation

HRID 1493643 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[CH3:15].[N:16]([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[NH2:16])=[CH:5][C:4]=1[CH3:15]

Participants

6

Reactant 2

HCID 23668193Sodium NitriteHCID 61506956HCID 61506956, compound2×

Product 1

HCID 54059198HCID 54059198, compoundYield 7.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

N-(4-methoxy-3-methylphenyl)glycine, methyl ester (Intermediate 96, 5 g, 0.0239 mol) was dissolved in a mixture of glacial acetic acid (45 ml) and water (3 ml) and the solution was cooled to ~5° C. To this was added a solution of sodium nitrite (1.7 g, 0.0251 mol) in water (5 ml) over 30 minutes and the reaction was stirred for one hour. Zinc dust (6 g, 0.093 mol) was added over 11/2 hours at the same low temperature and stirred at room temperature for 1 hour. The reaction was poured into water (150 ml) and extracted with ethyl acetate (2×100 ml). The organic extract was washed with 8% sodium bicarbonate solution until effervescence had ceased, then dried (MgSO4) and evaporated to give a yellow oil. This was purified by flash column chromatography on silica (Merck 9385; 100 g) eluting with ether-hexane 1:1 to give the title compound as an orange oil (0.4 g, 7%).

Workup

  1. temperaturethe solution was cooled to ~5° C
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. extractionThe organic extract
  5. washwas washed with 8% sodium bicarbonate solution until effervescence
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a yellow oil
  9. customThis was purified by flash column chromatography on silica (Merck 9385; 100 g)
  10. washeluting with ether-hexane 1:1

Sources & evidence

ORD record
ord-89f110cef143459198ce8e7500826483
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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