Hydrochloric Acid → 2-(2,4-Dinitrobenzamido)acetic acid

HRID 1399428

Reaction equation

HRID 1399428 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].[N+:12]([C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18])([O-:14])=[O:13].Cl>O.O1CCOCC1>[N+:12]([C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:16]=1[C:17]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:18])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10340Sodium CarbonateHCID 884012,4-Dinitrobenzoyl chloride

Product 1

HCID 446655292-(2,4-Dinitrobenzamido)acetic acidYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice cold suspension of glycine (1.01 g, 13.56 mmol) in water (20 mL) was added Na2CO3 (1.437 g, 13.56 mmol) and stirred for 10 min. A solution of 2,4-dinitrobenzoyl chloride (prepared from 2,4-dinitrobenzoic acid, 2.3 g with SOCl2, 20 mL) in dioxane (20 mL) was added to the above solution and stirred at rt for 4 h. The reaction mixture was diluted with ice cold water and acidified with cold dil. HCl (pH: 6.0). The solution was extracted with EtOAc (5×100 mL) and the combined organic layer was dried over anhyd Na2SO4 and filtered. The solution was evaporated and the residue was chromatographed over silica gel column using chloroform:methanol (95:5) as eluents to give the product as a white color solid (2.5 g, 85%), mp 188-190° C. 1H NMR (400 MHz, DMSO-d6): δ 12.79 (1H, br s), 9.29 (1H, t, J=5.4 Hz), 8.77 (1H, d, J=2.0 Hz), 8.64 (1H, dd, J=8.4, 2.0 Hz), 7.89 (1H, d, J=8.4 Hz), 3.99 (2H, d, J=6.0 Hz); LC-MS (negative ion mode): m/z 268 (M−H)−.

Workup

  1. stirringstirred at rt for 4 h
  2. additionThe reaction mixture was diluted with ice cold water
  3. extractionThe solution was extracted with EtOAc (5×100 mL)
  4. dry with materialthe combined organic layer was dried over anhyd Na2SO4
  5. filtrationfiltered
  6. customThe solution was evaporated
  7. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-392e87f112624ab5a96d4a1ca166b820
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Linked notes

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