Ethanol → HCID 59256628, compound

HRID 640800Notes

Reaction equation

HRID 640800 reaction equation
O.[Sn](Cl)Cl.[Cl:5][C:6]1[CH:21]=[C:20]([Cl:22])[C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:11])=[C:8]([N+:23]([O-])=O)[C:7]=1[OH:26].CCO.C([O-])(O)=O.[Na+]>CC(O)=O>[NH2:23][C:8]1[C:7]([OH:26])=[C:6]([Cl:5])[CH:21]=[C:20]([Cl:22])[C:9]=1[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 43835034Tin dichloride dihydrateHCID 59256555HCID 59256555, compound

Product 1

HCID 59256628HCID 59256628, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of tin (II) chloride hydrate (8.8 g, 0.039 mol), 4,6-dichloro-N-(4-fluorophenyl)-3-hydroxy-2-nitrobenzamide (2.7 g, 0.008 mol) and EtOH (70 mL) was heated at 70° C. for 1 h and left to cool to room temperature. The mixture was poured onto ice, basified to pH 8 (sat'd NaHCO3), and stirred at room temperature for 1.5 h before re-acidifying to pH 6.5 with glacial HOAc. The suspension was filtered; the filtrate was concentrated to give a beige solid. The beige solid was combined with the filter cake and extracted with hot ethyl acetate (5×). The extracts were combined to provide 2-amino-4,6-dichloro-N-(4-fluorophenyl)-3-hydroxybenzamide as a solid (2.0 g, 79%).

Workup

  1. waitleft
  2. temperatureto cool to room temperature
  3. additionThe mixture was poured onto ice
  4. filtrationThe suspension was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give a beige solid
  7. extractionextracted with hot ethyl acetate (5×)

Sources & evidence

ORD record
ord-454c912c27204ea2a4ff8d4bd4b6154e
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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