Hydrochloric Acid → 2,4-Difluoro-N-(3-amino-4-fluorophenyl)benzamide

HRID 1591864

Reaction equation

HRID 1591864 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)=[O:5].O.O.Cl[Sn]Cl.Cl>C(O)C>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([NH2:14])[CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 92126042,4-difluoro-N-(4-fluoro-3-nitrophenyl)benzamide

Product 1

HCID 167726472,4-Difluoro-N-(3-amino-4-fluorophenyl)benzamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a method similar to Preparation 14 using 2,4-Difluoro-N-(4-fluoro-3-nitrophenyl)benzamide (Preparation 13) (1.0 g, 3.38 mmol), SnCl2.2H2O (3.8 g, 16.9 mmol), ethanol (25 mL), and concentrated HCl (25 mL), gives the title intermediate (803 mg, 89% yield): mass spectrum (ion spray): m/z=267.0 (M+1).

Sources & evidence

ORD record
ord-6fd2e79dce084d659fc2e4a7c3fb9746
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Linked notes

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