Hydrochloric Acid → HCID 70507074, compound

HRID 2418712Notes

Reaction equation

HRID 2418712 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=O.C[Si]([C:25]#[N:26])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:33]>>[ClH:33].[NH2:26][CH2:25][C:7]1[C:8]2[C:3](=[C:2]([NH2:1])[C:11]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 82115Trimethylsilyl cyanideHCID 12392434HCID 12392434, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 70507074HCID 70507074, compound

Procedure

5-amino-6-benzyloxy-1,2,3,4-tetrahydro-1-naphthalenone (such as that disclosed in U.S. Pat. No. 4,035,512) is reacted with trimethylsilylcyanide followed by lithium aluminum hydride. The resultant 1-hydroxy-1- aminomethyl compound is dehydrated with HCl to give 1-aminomethyl-5-amino-6-benzyloxy-3,4-dihydronaphthalene HCl. This latter compound is reacted with trifluoro acetic anhydride to give 1-trifluoroacetylaminomethyl-5-amino-6-benzyloxy-3,4-dihydronaphthalene. This latter compound is formylated with formic acid and acetic anhydride and the trifluoroacetyl group is removed with Na2CO3 to yield 1-aminomethyl-5-formamido 6-benzyloxy-3,4-dihydronaphthalene HCl.

Sources & evidence

ORD record
ord-c57777168ad542418d67d55b7a03949a
Source dataset
uspto-grants-1984_09
Patent number
US04473586

Reaction notes

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