HCID 13398586, compound → HCID 23458286, compound

HRID 903967Notes

Reaction equation

HRID 903967 reaction equation
N[C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([CH:12]1[O:17][CH2:16][C:15](=[O:18])[N:14]([CH3:19])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N([O-])=[O:25].[Na+]>OS(O)(=O)=O.O>[OH:25][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([CH:12]1[O:17][CH2:16][C:15](=[O:18])[N:14]([CH3:19])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 13398586HCID 13398586, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23458286HCID 23458286, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

10 g of 2-[α-(2-amino-phenoxy)-benzyl]-4-methyl-morpholin-5-one was dissolved at 0° C. in 32 ml of 35% H2SO4. At this temperature slow addition was made of 2.76 g of NaNO2 dissolved in 40 ml of H2O and the mixture was kept under stirring in cold conditions for 20 minutes. Still at 0° C. there was added 120 g of Cu(NO3)2 dissolved in 1000 ml of H2O and 4.2 g of Cu2O. After 5 minutes extraction was performed in cold conditions with ethyl acetate; the organic phase was washed to neutrality with a saturated aqueous solution of NaCl, dehydrated with sodium sulphate and evaporated to dryness. There was obtained a yellow oil which was separated by column chromatography on silica gel (phase: ethyl acetate/cyclohexane 2:1). There was obtained 6 g (Yield 60%) of 2-[α-(2-hydroxy-phenoxy)-benzyl]-4-methyl-morpholin-5 -one.

Workup

  1. additionAt this temperature slow addition
  2. extractionAfter 5 minutes extraction
  3. washthe organic phase was washed to neutrality with a saturated aqueous solution of NaCl
  4. customevaporated to dryness
  5. customThere was obtained a yellow oil which
  6. customwas separated by column chromatography on silica gel (phase: ethyl acetate/cyclohexane 2:1)

Sources & evidence

ORD record
ord-9a29066c41504a21bb13e267c57e974b
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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