Sodium Bicarbonate → HCID 14459000, compound

HRID 569812Notes

Reaction equation

HRID 569812 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[N+:16]([O-])=O)=[C:4]([F:22])[CH:3]=1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[C:8]([NH:7][CH2:6][C:5]1[CH:20]=[CH:21][C:2]([Br:1])=[CH:3][C:4]=1[F:22])=[O:19]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 14458989HCID 14458989, compound

Product 1

HCID 14459000HCID 14459000, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-bromo-2-fluorobenzyl)-4-fluoro-2-nitrobenzamide (4.79 g) and stannous chloride (12.24 g) in ethanol (26 ml) was stirred at 70°-80° C. for 30 minutes under an atmosphere of nitrogen. After cooling, the reaction mixture was poured into ice-cold water and neutralized with aqueous saturated sodium bicarbonate. The resulting precipitates were filtered off and washed with ethyl acetate. The filtrate was extracted with ethyl acetate and the extract was washed with water and dried. Removal of the solvent gave 2-amino-N-(4-bromo-2-fluorobenzyl)-4-fluorobenzamide (3.58 g).

Workup

  1. temperatureAfter cooling
  2. customThe resulting precipitates
  3. filtrationwere filtered off
  4. washwashed with ethyl acetate
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with water
  7. customdried
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-3fd5013f3337497a95a9a1f40885f884
Source dataset
uspto-grants-1988_03
Patent number
US04734419

Reaction notes

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