2-Phenoxyethanamine → N4-(2-phenoxyethyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 497781Notes

Reaction equation

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

Participants

Reactant 2

HCID 156512-Phenoxyethanamine

HCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 53680712N4-(2-phenoxyethyl)-3-nitro[1,5]naphthyridin-4-amineYield 88.6%

Procedure

Using the general method of Example 76, 4-chloro-3-nitro[1,5]naphthyridine (5.0 g, 24 mmol) was reacted with 2-phenoxyethylamine (3.5 mL, 27 mmol) to provide 6.6 g of N4-(2-phenoxyethyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid, m.p. 107-108° C. Analysis: Calculated for C16H14N4O3: %C, 61.93; %H, 4.55; %N, 18.05; Found: %C, 61.99; %H, 4.58; %N, 18.42. 1H NMR (300 MHz, DMSO): δ 10.25 (broad s, 1H), 9.39 (broad s, 1H), 8.81 (dd, J=4.1, 1.7 Hz, 1H), 8.25 (dd, J=8.5, 1.7 Hz, 1H), 7.67 (dd, J=8.5, 4.1 Hz, 1H), 7.34-7.26 (m, 2H), 7.01-6.96 (m, 3H), 4.89 (broad s, 2H), 4.35 (t, J=5.1 Hz, 2H); MS (EI): m/e 310.1065 (310.1065 calc'd for C16H14N4O3).

Sources & evidence

ORD record: ord-2678c53977c14c9cb3fcb7f76f67350d
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949646B2

Reaction notes

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