Sodium borohydride → HCID 12439096, compound

HRID 972511Notes

Reaction equation

HRID 972511 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+]>[Pd].C1(OC)C=CC=CC=1>[CH3:18][O:17][C:15](=[O:16])[CH2:14][C:3]1[CH:2]=[C:11]2[C:6]([CH:7]=[C:8]([O:12][CH3:13])[N:9]=[CH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21404781HCID 21404781, compound

Product 1

HCID 12439096HCID 12439096, compound

Reagents, catalysts & solvents 1

HCID 86735127HCID 86735127, compoundCatalyst

Procedure

7-Aza-6-methoxy-1-tetralone is reacted with glyoxylic acid to provide 7-aza-2-carboxy-hydroxymethyl-6-methoxy-1-tetralone and this compound is dehydrated by heating in base to provide 7-aza-2-carboxy-methylidene-6-methoxy-1-tetralone. Saturation of the double bond with zinc in acetic acid followed by 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 on Carbon/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-methyl-acetate and hydrolysis of this ester provides 3-methoxy-2-azanaphthalene-7-α-methylacetic acid.

Sources & evidence

ORD record
ord-08d126c0aed349688d15baeec53fa571
Source dataset
uspto-grants-1977_10
Patent number
US04053476

Reaction notes

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