Methyl cyanoacetate → 2-Amino-4-benzyl-3-carbomethoxy-5-hydroxynaphtho[1,2-b]furan

HRID 5488

Reaction equation

[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH2:8]([C:15]1[C:16](=[O:26])[C:17]2[C:22]([C:23](=[O:25])[CH:24]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[NH2:2][C:1]1[O:25][C:23]2[C:22]3[C:17]([C:16]([OH:26])=[C:15]([CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:24]=2[C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[CH:18][CH:19]=[CH:20][CH:21]=3

Participants

Reactant 2

HCID 7747Methyl cyanoacetate

HCID 30156581,4-Naphthalenedione, 2-(phenylmethyl)-

Product 1

HCID 197960222-Amino-4-benzyl-3-carbomethoxy-5-hydroxynaphtho[1,2-b]furan

Procedure

The title compound was prepared by reaction of methyl cyanoacetate with 2-benzyl-1,4-naphthoquinone following the procedure outlined for example 1. Obtained as tan crystals (55%); m.p. 170°-171° C.; 1H NMR (CDCl3): 3.66(s, 3H), 4.05(s,2H), 5.07(s,2H), 7.17-7.53(m, 8H), 7.98(d, 1H), 8.10(d,1H); IR (nujol): 3309, 3479, 3566, 1725, 1604; Chemical ionization mass spectrum m/z (rel. intensity) 348 (M+H, 100); calculated for C21H17NO4C 72.61, H 4.93; measured C 72.79, H 4.68, N 4.00.

Sources & evidence

ORD record: ord-684753ba46a94919aea239a16efe8f16
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244917

Linked notes

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