Benzylamine → Ethyl 4-benzylamino-2-fluoro-5-nitro-benzoate

HRID 1406538Notes

Reaction equation

HRID 1406538 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:20]=[C:19](F)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C1COCC1>[CH2:1]([NH:8][C:19]1[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([F:9])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Product 1

HCID 67230873Ethyl 4-benzylamino-2-fluoro-5-nitro-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Benzylamine (7.6 mL, 69 mmol) in 30 mL THF was added to ethyl 2,4-difluoro-5-nitro-benzoate (16.0 g, 69 mmol) in 270 mL THF with TEA (19.7 mL, 140 mmol) under stirring at 0° C. The mixture was stirred for 3.5 h at ambient temperature. The mixture was concentrated i.vac., the residue stirred with water, filtered off, washed with water and dried.

Workup

  1. stirringThe mixture was stirred for 3.5 h at ambient temperature
  2. concentrationThe mixture was concentrated i.vac
  3. stirring, the residue stirred with water
  4. filtrationfiltered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-bfd7948911d348dda156b57de7dd94f3
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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