3-Ethylisoquinolin-5-amine → (RS)-3-[(3-ethylisoquinol-5-yl)imino]-9,9a-dihydrothiazolo[3,4-a]indole

HRID 262125Notes

Reaction equation

HRID 262125 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][CH3:13])[N:6]=[CH:7]2.[I-].CS[C:17]1[S:18][CH2:19][CH:20]2[CH2:28][C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:21]=12>>[CH2:12]([C:5]1[N:6]=[CH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([N:1]=[C:17]1[N:21]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[CH2:28][CH:20]3[CH2:19][S:18]1)[CH:11]=[CH:10][CH:9]=2)[CH3:13]

Participants

3

Reactant 2

HCID 213201443-Ethylisoquinolin-5-amineHCID 21320148(RS)-3-Methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide

Product 1

HCID 21320153(RS)-3-[(3-ethylisoquinol-5-yl)imino]-9,9a-dihydrothiazolo[3,4-a]indoleYield 70.6%

Procedure

Following the procedure of Example 1 but starting with 5-amino-3-ethylisoquinoline (3.3 g) and (RS)-3-methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide (6.3 g), (RS)-3-[(3-ethylisoquinol-5-yl)imino]-9,9a-dihydrothiazolo[3,4-a]indole (4.4 g) is obtained, after recrystallisation from ethanol (40 cc), in the form of white crystals melting at 142° C.

Sources & evidence

ORD record
ord-ea91d975393649b59bf779dfd2616974
Source dataset
uspto-grants-1979_05
Patent number
US04153699

Reaction notes

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