Hydrochloric Acid → 1-aminomethyl-7-methoxy-3,4-dihydronaphthalene HCl

HRID 2418705Notes

Reaction equation

HRID 2418705 reaction equation
COC1C=C2C(CCCC2=O)=CC=1.C[Si](C#N)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:26][CH2:27][C:28]1(O)[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=2)[CH2:31][CH2:30][CH2:29]1.[ClH:41]>C(O)C>[ClH:41].[NH2:26][CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=2)[CH2:31][CH2:30][CH:29]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 82115Trimethylsilyl cyanideHCID 12262631HCID 12262631, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 122626331-aminomethyl-7-methoxy-3,4-dihydronaphthalene HCl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 g. of 7-methoxy-1,2,3,4-tetrahydro-1-naphthalenone is reacted with trimethylsilylcyanide and then with lithium aluminum hydride as described in Example 1 to yield 28 g. of 1-aminomethyl-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. This compound is treated with HCl in ethanol as described in Example 3 to give 1-aminomethyl-7-methoxy-3,4-dihydronaphthalene HCl; m.p. 174°-175° C.

Workup

  1. customto yield 28 g

Sources & evidence

ORD record
ord-7259cc4d32054aae8394cc9cc2cc0b82
Source dataset
uspto-grants-1984_09
Patent number
US04473586

Reaction notes

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