2-Fluoro-5-nitrobenzoic acid → HCID 43610334, compound

HRID 1022490Notes

Reaction equation

HRID 1022490 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O:14]1[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]1>CN(C=O)C>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:20][CH:17]2[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 2809972-Fluoro-5-nitrobenzoic acidHCID 4192234-Aminotetrahydropyran

Product 1

HCID 43610334HCID 43610334, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.1 g of 2-fluoro-5-nitrobenzoic acid and 6.21 g of tetrahydro-2H-pyran-4-amine in 5 ml of DMF is irradiated in a microwave field for 15 minutes at 100° C. The mixture is irradiated a second time for 15 minutes at 100° C. The same reaction is repeated on identical amounts of reagents. All the reaction mixtures are pooled and the solvent is evaporated off under reduced pressure. The residue is recrystallized from EtOAc to give 6 g of expected product.

Workup

  1. customis irradiated in a microwave field for 15 minutes at 100° C
  2. customThe mixture is irradiated a second time for 15 minutes at 100° C
  3. customThe same reaction
  4. customAll the reaction mixtures
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe residue is recrystallized from EtOAc

Sources & evidence

ORD record
ord-946d07d3a9c34a1f931e4811f47b9c7a
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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