Methyl 3-amino-4-fluorobenzoate → 3-Amino-N-(2-tert-butoxyethyl)-4-fluorobenzamide

HRID 335316Notes

Reaction equation

HRID 335316 reaction equation
[C:1]([O:5][CH2:6][CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[NH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[F:20])[C:13](OC)=[O:14]>C1COCC1>[NH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[F:20])[C:13]([NH:8][CH2:7][CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14]

Participants

4

Reactant 2

HCID 12541234Methyl 3-amino-4-fluorobenzoateHCID 219146142-(Tert-butoxy)ethanamine

Product 1

HCID 866956823-Amino-N-(2-tert-butoxyethyl)-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture comprising 2-tert-butoxyethanamine (1.2 g, 5.12 mmol, 50% w/w) and methyl 3-amino-4-fluorobenzoate (0.866 g, 5.12 mmol) in THF (10 ml) was treated with TBD (0.713 g, 5.12 mmol) and heated at 90° C. for 16 hrs. After cooling to RT, the solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic portion was separated and washed with 10% aq citric acid (×2), NaHCO3 (sat. aq), brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title compound as a clear oil;

Workup

  1. temperatureAfter cooling to RT
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. customThe organic portion was separated
  5. washwashed with 10% aq citric acid (×2), NaHCO3 (sat. aq), brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-d08b0bf3bb674261909543edc893948b
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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