Sodium Hydroxide → 2-amino-4-bromo-N-(4-bromo-2-fluorobenzyl)benzamide

HRID 1639299

Reaction equation

HRID 1639299 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=2[F:17])=[O:7])=[C:4]([N+:20]([O-])=O)[CH:3]=1.[OH-].[Na+]>C(O)(=O)C.[Fe]>[NH2:20][C:4]1[CH:3]=[C:2]([Br:1])[CH:19]=[CH:18][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[F:17])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 144589874-bromo-N-(4-bromo-2-fluorobenzyl)-2-nitrobenzamide

Product 1

HCID 144589952-amino-4-bromo-N-(4-bromo-2-fluorobenzyl)benzamideYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-N-(4-bromo-2-fluorobenzyl)-2-nitrobenzamide (3.4 g) and iron (1.45 g) in acetic acid (66 ml) was stirred at 100° C. for 30 minutes. After cooling, iron was filtered off. The filtrate was evaporated to give a residue, which was made alkaline with aqueous 1N sodium hydroxide and extracted with ethyl acetate. The extract was washed with water and dried. Removal of the solvent gave 2-amino-4-bromo-N-(4-bromo-2-fluorobenzyl)benzamide (3.10 g).

Workup

  1. temperatureAfter cooling
  2. filtrationiron was filtered off
  3. customThe filtrate was evaporated
  4. customto give a residue, which
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-4eea3f8d26614eabaecd02eb0fccda4f
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Linked notes

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