Hydrochloric Acid → Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

HRID 508831Notes

Reaction equation

HRID 508831 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH:14]=[N:15]O)=[CH:4][CH:3]=1.Cl>CO.[Zn]>[NH2:15][CH2:14][C:5]1[C:6]([F:13])=[C:7]([C:2]([Cl:1])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 76800184Ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate

Product 1

HCID 58483233Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoateYield 79.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate (0.800 g, 3.26 mmol) in MeOH (5 mL) was added Zn (0.850 g, 13.06 mmol), followed by dropwise addition of conc. HCl (catalytic) and the reaction mixture was heated at 60° C. for 2-3 h. Excess of solvent was removed under vacuum and the residue was diluted with water and basified with NaHCO3, extracted with EtOAc and concentrated to afford 0.600 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.31 (t, J=7.2 Hz, 3H), 3.76 (s, 2H), 4.38 (q, J=6.9 Hz, 2H), 7.41 (d, J=8.1 Hz, 1H), 7.65 (t, J=8.1 Hz, 1H).

Workup

  1. customExcess of solvent was removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-021ec19d312e4e1f9b4eb7039ee5d178
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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