3-Pyridinemethanamine → 3-Fluoro-4-nitro-N-(3-pyridylmethyl)benzamide

HRID 72767

Reaction equation

HRID 72767 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH2:21])[CH:15]=1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(=O)([O-])O.[Na+].C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH:21][CH2:20][C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)=[O:7]

Participants

8

Reactant 5

HCID 310183-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 591986673-Fluoro-4-nitro-N-(3-pyridylmethyl)benzamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-Fluoro-4-nitrobenzoic acid 2.78 g, 3-pyridylmethylamine 1.55 mL, N,N-diisopropylethylamine 2.61 mL, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 4.31 g, 1-hydroxybenzotriazole monohydrate 2.98 g and acetonitrile 39 mL were mixed and stirred for 20 hours. The reaction liquid was poured in saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine by the order stated, and dried over magnesium sulfate. Distilling the solvent off, 4.09 g of the title compound was obtained.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine by the order
  4. dry with materialdried over magnesium sulfate
  5. distillationDistilling the solvent off, 4.09 g of the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-b2ee502842fb410a956edc914c523915
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Linked notes

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