Trifluoroacetic acid → 3-Nitro-5,6,7,8-tetrahydro-1,6-naphthyridine

HRID 887672Notes

Reaction equation

HRID 887672 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=2[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:18]([C:12]1[CH:13]=[N:14][C:15]2[CH2:16][CH2:17][NH:8][CH2:9][C:10]=2[CH:11]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10934795tert-Butyl 3-nitro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 142970643-Nitro-5,6,7,8-tetrahydro-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-nitro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (6.14 g, 22 mmol) in CH2Cl2 (60 mL) was added TFA (7 mL). The reaction was stirred for 18 h at RT. After evaporation of the solvent, the residue was taken into water and neutralized with saturated NaHCO3 aqueous solution. The solid was filtered and washed with cold water and dried. The solid was recrystallized from CH3CN to give desired title compound as pale white solid. MS (ES+): 180.1 (M+H)+. Calc'd for C8H9N3O2—179.07.

Workup

  1. customAfter evaporation of the solvent
  2. filtrationThe solid was filtered
  3. washwashed with cold water
  4. customdried
  5. customThe solid was recrystallized from CH3CN

Sources & evidence

ORD record
ord-3061eb9e83f74aa99a9698f324ea0669
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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