Hydrochloric Acid → Ethyl N-methyl-N-(4-nitrosophenyl)glycinate

HRID 1005270

Reaction equation

HRID 1005270 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[N:16]([O-])=[O:17].[Na+].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][N:2]([C:9]1[CH:10]=[CH:11][C:12]([N:16]=[O:17])=[CH:13][CH:14]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 265936(Methyl-phenyl-amino)-acetic acid ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 12038854Ethyl N-methyl-N-(4-nitrosophenyl)glycinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 15.5 g (80 mmol) of ethyl N-methyl-N-phenylglycinate in 80 g of ice and 40 mL of conc.HCl was stirred at 0-5° while a solution of 6 g (87 mmol) of NaNO2 in 40 mL of water was added dropwise over 30 min. After stirring at this temp. for 1 hr, a solution of 27 g (250 mmol) of Na2CO3 in 150 mL of water was added dropwise with cooling. The green solid was collected, washed with cold water, extracted into CH2Cl2, passed thorugh silica with CH2Cl2 to remove an impurity, and the product eluded with 10% ethyl acetate/CH2Cl2 to give 14.7 g (66 mmol, 83%) mp 55-56° after washing with 10% ethyl acetate/hexane. Anal. C11H14N2O3 (222): Calcd.: C,59.45; H,6,35; N,12.60. Found: C,59.46; H,6.14; N,12.49. MS(FD) m/z 222. 1H NMR(CDCl3)δ: 7.8,broad s,2H,ArH; 6.69,d,2H,ArH; 4.22,q,2H,CH2 --O; 4.20,s,2H,CH2 --N; 3.23,s,3H,CH3 --N; 1.27,t,3H,CH3 --C.

Workup

  1. additionwas added dropwise over 30 min
  2. temperaturewith cooling
  3. customThe green solid was collected
  4. washwashed with cold water
  5. extractionextracted into CH2Cl2
  6. customto remove an impurity
  7. customto give 14.7 g (66 mmol, 83%) mp 55-56°
  8. washafter washing with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-bd1b2f43f2a6466e9d2d95111e299170
Source dataset
uspto-grants-2000_04
Patent number
US06054260

Linked notes

Loading…