3-Methylisoquinolin-5-amine → HCID 22807723, compound

HRID 262123Notes

Reaction equation

HRID 262123 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]=[CH:7]2.[I-].CS[C:16]1[S:17][CH2:18][C@@H:19]2[CH2:27][C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:20]=12>>[CH3:12][C:5]1[N:6]=[CH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([N:1]=[C:16]1[N:20]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[CH2:27][C@H:19]3[CH2:18][S:17]1)[CH:11]=[CH:10][CH:9]=2

Participants

3

Reactant 2

HCID 122120553-Methylisoquinolin-5-amineHCID 70610289HCID 70610289, compound

Product 1

HCID 22807723HCID 22807723, compoundYield 72.9%

Procedure

Following the procedure of Example 1 but starting with 5-amino-3-methylisoquinoline (6.0 g) and (S)-3-methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide (12.0 g), (S)-3-[(3-methylisoquinol-5-yl)imino]-9,9a-dihydrothiazolo[3,4-a]indole (8.3 g) is obtained, after recrystallisation from ethanol, in the form of white crystals melting at 182° C. [α]D20 =-92.5±1.5° (c=1, chloroform)

Sources & evidence

ORD record
ord-a6b77f5dcfe7426d87708e21c337071f
Source dataset
uspto-grants-1979_05
Patent number
US04153699

Reaction notes

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