Hydrochloric Acid → 2-({4-[(Carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid

HRID 2367088Notes

Reaction equation

HRID 2367088 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].Cl.C([O:25][C:26](=[O:29])[CH2:27][NH2:28])C.[OH-].[K+].Cl>>[C:26]([CH2:27][NH:28][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20])([OH:29])=[O:25]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 665622-(4-Chloro-3-nitrobenzoyl)benzoic acidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 670441602-({4-[(Carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acidYield 76%

Conditions

Temperature
90 °C

Procedure

A suspension of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (0.31 g 1.00 mmol) and glycine ethyl ester hydrochloride (0.69 g, 5.00 mmol) in a solution of 4M aqueous potassium hydroxide (3.8 mL, 15.0 mmol) was heated to 90° C. for 15 hours. The reaction mixture was cooled to room temperature and it was treated with 2M aqueous hydrochloric acid to adjust the pH to ˜5. It was partitioned with ethyl acetate (50 mL) and the organic layer was washed with brine and dried over anhydrous sodium sulfate. Filtration and concentration of the solvent gave 2-({4-[(carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid (0.26 g, 76% yield) as a white residue. MS (EI) for C16H12N2O7: 342 (M−).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customIt was partitioned with ethyl acetate (50 mL)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration of the solvent

Sources & evidence

ORD record
ord-49a1d5b3aa3e4a21a0b5df337edc1062
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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