HCID 68283673, compound → HCID 68283754, compound

HRID 1527459Notes

Reaction equation

HRID 1527459 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([F:14])=[C:7]([Br:15])[CH:6]=1)[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:6]=[C:7]([Br:15])[C:8]([F:14])=[C:9]([NH2:11])[CH:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68283673HCID 68283673, compound

Product 1

HCID 68283754HCID 68283754, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-4-fluoro-5-nitro-benzoic acid ethyl ester (20 g, 2.2 mol) and 3 g of Raney-Ni in EtOH (250 mL) was hydrogenated at RT (1 atm) overnight. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was washed with petrol ether to afford the title compound as a white solid. (400 MHz, DMSO-d6): δ (ppm) 7.38 (dd, 1H), 7.26 (dd, 1H), 5.81 (s, 2H), 4.26 (q, 2H), 1.29 (t, 3H).

Workup

  1. customwas hydrogenated at RT
  2. custom(1 atm) overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washthe residue was washed with petrol ether

Sources & evidence

ORD record
ord-0d1b211634874e9f93f8dbad9e78c001
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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