3-Aminopyridine → (S)-7-Nitro-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 461820Notes

Reaction equation

HRID 461820 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][C:12]([N+:17]([O-:19])=[O:18])=[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:12]1[CH:13]=[CH:14][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]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 86735299(S)-3-Methylthio-7-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 22800664(S)-7-Nitro-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 88.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-3-Methylthio-7-nitro-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (23 g.) is added to a solution of 3-aminopyridine (11 g.) in pyridine (400 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 (1,500 cc.) and water (500 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 a mixture of acetonitrile and ethanol (1:1 by volume). (S)-7-Nitro-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (16.2 g.) is thus obtained in the form of yellow crystals melting at 234° 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 a mixture of acetonitrile and ethanol (1:1 by volume)

Sources & evidence

ORD record
ord-17a45e6e5417418e82c4d1ae03a2767b
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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