Hydrochloric Acid → HCID 18980356, compound

HRID 2392709Notes

Reaction equation

HRID 2392709 reaction equation
C([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:14]=1[N+:21]([O-:23])=O)=[O:11])(=O)C1C=CC=CC=1.Cl>[OH-].[Na+]>[Cl:20][C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][C:17]=1[Cl:19])[NH:12][C:10](=[O:11])[CH:9]=[N+:21]2[O-:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18980359HCID 18980359, compound

Product 1

HCID 18980356HCID 18980356, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the N-(benzoylacetyl)-4,5-dichloro-2-nitroaniline (0.351 g, 1 mmol) in 20% NaOH (5 mL) was refluxed under stirring for 1 h. The mixture was cooled to room temperature and acidified with 2N HCl to pH 2 to form a precipitate. The precipitated product was filtered, washed with 2N HCl (3×20 mL), H2O (5×20 mL), ethanol (20 mL), and ether (20 mL), and then air dried to give 0.207 g (90%) of the title compound as a light brown powder: mp 278°-280° C. (H2O from DMSO); IR (KBr) 3450, 3104, 2934, 1693, 1593, 1517, 1412, 1270, and 890 cm-1 ; 1H NMR (DMSO-d6) δ7.50 (s, 1H), 7.95 (s, 1H), 8.23 (s, 1H), 12.45 (br.s, 1H, N--H); 13C NMR (DMSO-d6) δ118.09, 121.32, 125.79, 129.75, 130.31, 133.25, 135.50, 157.30; HPLC: 98.1%. HRMS Calcd for C8H4N2O2Cl2 : 229.9650. Found: 229.9660.

Workup

  1. temperaturewas refluxed
  2. customto form a precipitate
  3. filtrationThe precipitated product was filtered
  4. washwashed with 2N HCl (3×20 mL), H2O (5×20 mL), ethanol (20 mL), and ether (20 mL)
  5. customair dried

Sources & evidence

ORD record
ord-98fb10c518274118ac1d027a92355dd3
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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