3-Aminopyridine → HCID 22800660, compound

HRID 461812Notes

Reaction equation

HRID 461812 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>N1C=CC=CC=1>[N+:17]([C:14]1[C:15]2[CH2:16][C@H:7]3[CH2:6][S:5][C:4](=[N:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[N:8]3[CH2:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 86735298HCID 86735298, compound

Product 1

HCID 22800660HCID 22800660, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-3-Methylthio-9-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (6 g.) is added to a solution of 3-aminopyridine (3 g.) in pyridine (100 cc.). After 6 hours at a temperature of about 20° C., the mixture is concentrated to dryness under reduced pressure (25 mm. Hg). The residue is dissolved in a mixture consisting of methylene chloride (300 cc.) and water (200 cc.). The organic phase is decanted, washed with water (3 × 200 cc.), dried over magnesium sulphate, filtered and then concentrated to dryness. The residue obtained is recrystallised from acetonitrile (40 cc.) to give (S)-9-nitro-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (3.9 g.) in the form of white crystals melting at 144° C.

Workup

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (25 mm. Hg)
  2. dissolutionThe residue is dissolved in a mixture
  3. customThe organic phase is decanted
  4. washwashed with water (3 × 200 cc.)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue obtained
  9. customis recrystallised from acetonitrile (40 cc.)

Sources & evidence

ORD record
ord-68987ea2284b4dac987d304677c546e4
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

Loading…