Water → HCID 59441773, compound

HRID 1014387Notes

Reaction equation

HRID 1014387 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[CH3:17])[C:3](=[O:8])[CH2:4][N:5]([CH3:7])[CH3:6].[N:18]([O-:20])=[O:19].[Na+].O.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.CCOC(C)=O>[CH3:1][N:2]([C:9]1[CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[C:12]([O:15][CH3:16])=[CH:11][C:10]=1[CH3:17])[C:3](=[O:8])[CH2:4][N:5]([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 59442004HCID 59442004, compound

Product 1

HCID 59441773HCID 59441773, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of N1,N2,N2-trimethyl-N1-[2-methyl-4-(methyloxy)phenyl]glycinamide (4.9 g, 20.74 mmol) in TFA (20 mL) was treated with sodium nitrite (2.003 g, 29.0 mmol). The resulting thick mixture was stirred at rt. After 5 h water (20 mL) and EtOAc (200 mL) were added and the mixture was poured into a saturated NaHCO3 solution (300 mL). The layers were separated. The aqueous layer was treated with a few g of K2CO3 to obtain pH=8, then was extracted with EtOAc (2×125 mL) and CHCl3(2×125 mL). The combined organic layers were washed with a saturated NaCl solution (100 mL), dried (Na2SO4), concentrated onto Celite and purified by silica gel chromatography to obtain N1,N2,N2-trimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamide as an orange solid (1.87 g, 32% Yield). ESIMS (M+H)+=282.52.

Workup

  1. customThe layers were separated
  2. additionThe aqueous layer was treated with a few g of K2CO3
  3. customto obtain pH=8
  4. extractionwas extracted with EtOAc (2×125 mL) and CHCl3(2×125 mL)
  5. washThe combined organic layers were washed with a saturated NaCl solution (100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated onto Celite
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c3088c83d7194a3780afc855d304c8b4
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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