Trimethylsilyl cyanide → HCID 20445315, compound

HRID 2418711Notes

Reaction equation

HRID 2418711 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C[Si]([C:17]#[N:18])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[NH2:18][CH2:17][C:8]1([OH:12])[C:9]2[C:4](=[CH:3][C:2]([NH2:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 20445315HCID 20445315, compound

Procedure

6-amino-1,2,3,4-tetrahydro-1-naphthalenone is reacted with trimethylsilylcyanide followed by lithium aluminum hydride to obtain 1-aminomethyl-1-hydroxy-6-amino-1,2,3,4-tetrahydronaphthalene. This diamine is di-acetylated with acetic anhydride, chlorinated with chlorine and acetic acid, and then heated to dehydrate the alcohol. The resulting di-chloro-di-acetamide is hydrolyzed in HCl to obtain 1-aminomethyl-6-amino-5,7-dichloro-3,4-dihydronaphthalene HCl.

Sources & evidence

ORD record
ord-725fa07e82c248c1953b2646156b9b26
Source dataset
uspto-grants-1984_09
Patent number
US04473586

Reaction notes

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