Sodium borohydride → HCID 12439096, compound
Reaction equation
O[CH:2]1[C:11]2[CH:10]=[N:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=2[CH2:5][CH2:4][CH:3]1[CH2:14][C:15]([O:17][CH3:18])=[O:16].[BH4-].[Na+]>>[CH3:13][O:12][C:8]1[N:9]=[CH:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:2]=2Participants
Procedure
5-Aza-6-loweralkoxytetralone (Tetrahedron Letters No. 1, pp. 87-90, 1966) and 7-aza-6-loweralkoxytetralone (Tetrahedron Letters No. 9, 623, 1975) are suitable precursors for initiating the above indicated reaction Scheme I. In accordance with Scheme I 7-aza-6-methoxytetralone is reacted with glyoxylic acid to provide 7-aza-2-carboxyhydroxymethyl-6-methoxy-1-tetralone and this compound is dehydrated by heating in base to provide 7-aza-6-methoxy-α-carboxymethylidene-1-tetralone. This latter tetralone is reduced with zinc/acetic acid to provide 7-aza-2-carboxymethyl-6-methoxy-1-tetralone and acid catalysed esterification with methanol and sulfuric acid provides 7-aza-6-methoxy-2-methoxycarbonylmethyl-1-tetralone. 7-Aza-6-methoxy-2-methoxycarbonylmethyl-1-tetralone to methyl 8-hydroxy-3-methoxy-5,6,7,8-tetrahydro-2-azanaphthalene-7-acetate by reaction with sodium borohydride and reaction of this product with Pd(C)/anisole provides methyl 3-methoxy-2-azanaphthalene-7-acetate which is alkylated with methyl iodide and base to provide methyl 3-methoxy-2-azanaphthalene-7-α-methylacetate and hydrolysis of this ester provides 3-methoxy-2-azanaphthalene-7 -α -methylacetic acid.
Sources & evidence
- ORD record
- ord-59931cd919604dcb96b7f3b244964b1d
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03991061
Reaction notes
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