5-Aminoquinoline → (S)-3-(quinol-5-yl-imino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 1902546Notes

Reaction equation

[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2>>[N:23]1[C:24]2[C:19](=[C:18]([N:17]=[C:4]3[N:8]4[CH2:9][C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=5[CH2:16][C@H:7]4[CH2:6][S:5]3)[CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Reactant 2

HCID 119115-Aminoquinoline

HCID 12874874HCID 12874874, compound

Product 1

HCID 22822250(S)-3-(quinol-5-yl-imino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 90.3%

Procedure

By following the procedure of Example 2, but using (S)-3-methylthio-1,5,10,10a-tetrahydrothiazolo-[3,4-b]isoquinolinium iodide (18.2 g) and 5-aminoquinoline (14.4 g) as the starting materials, (S)-3-(quinol-5-yl-imino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (15.0 g) is obtained in the form of light beige crystals, m.p.=194° C.

Sources & evidence

ORD record: ord-811fd73103f24d9fb53a677f39a7790f
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04363909

Reaction notes

Loading…