Hydrochloric Acid → 2-Chloro-2-hydroxyiminoacetic acid ethyl ester

HRID 2425964Notes

Reaction equation

HRID 2425964 reaction equation
N[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[N:8]([O-:10])=O.[Na+].[ClH:12]>O>[Cl:12]/[C:2](=[N:8]\[OH:10])/[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12176Glycine ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl esterYield 42.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of compound ethyl 2-aminoacetate (30.0 g, 0.24 mol) in water (50 mL) and 36% HCl (36 mL) was added dropwise a solution of NaNO2 in water (100 mL) at −5° C. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to give compound N.3, (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (17.4 g, 42.1%). 1H NMR (DMSO-d6) δ 13.41 (s, 1H), 4.25 (q, 2H), 1.24 (t, 3H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89802d6d9d1849c581c0dd869c92bde4
Source dataset
uspto-grants-2011_06
Patent number
US07968536B2

Reaction notes

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