Nitrogen → HCID 23458271, compound

HRID 1679976Notes

Reaction equation

HRID 1679976 reaction equation
N[C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]([O:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].N([O-])=[O:25].[Na+].N#N>Cl.O>[OH:25][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]([O:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 947NitrogenHCID 23458284HCID 23458284, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23458271HCID 23458271, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 8 g of ethyl 3-(2-amino-phenoxy)-3-phenyl-2-methoxy-propionate, dissolved in 23% HCl (11.6 ml) at 4°-5° C., water (30 ml) was added and, always under cooling, a solution of NaNO2 (1.73 g) dissolved in water (30 ml) was slowly dropped. The solution was stirred at room temperature for 30 minutes and then heated at 50° C. for 15 minutes; evolution of N2 was noted. After extraction with CH2Cl2 and appropriate washings, the CH2Cl2 was evaporated to dryness so obtaining an oil, which was separated by column chromatography to give 4.0 g of ethyl 3-(2-hydroxy-phenoxy)-3-phenyl-2-methoxy-propionate (50%).

Workup

  1. temperaturealways under cooling
  2. additionwas slowly dropped
  3. temperatureheated at 50° C. for 15 minutes
  4. extractionAfter extraction with CH2Cl2 and appropriate washings
  5. customthe CH2Cl2 was evaporated to dryness
  6. customso obtaining an oil, which
  7. customwas separated by column chromatography

Sources & evidence

ORD record
ord-71a408189f4a4f5896b69f114db0e85c
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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